Benzamidoacetonitriles and their use as antiparasitics

ABSTRACT

The invention relates to compounds of the general formula 
                         
and optionally the enantiomers thereof. These compounds have advantageous pesticidal properties. They are especially suitable for controlling parasites in warm-blooded animals.

This application is a National Phase Application under

371 of International Application Number PCT/EP02/005294 filed on May 14, 2002.

The present invention relates to new benzamidoacetonitrile compounds of formula

wherein Ar₁ and Ar₂, independently of one another, signify unsubstituted phenyl or phenyl which is substituted once or many times, whereby the substituents may be independent of one another and are selected from the group comprising halogen, nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₂-C₆-alkenyl, halo-C₂-C₆-alkenyl, C₂-C₆-alkinyl, C₃-C₆-cycloalkyl, C₂-C₆-alkenyloxy, halo-C₂-C₆-alkenyloxy, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio, C₁-C₆-alkylsulfonyloxy, halo-C₁-C₆-alkylsulfonyloxy, C₁-C₆-alkylsulfinyl, halo-C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, halo-C₁-C₆-alkylsulfonyl, C₂-C₆-alkenylthio, halo-C₂-C₆-alkenylthio, C₂-C₆-alkenylsulfinyl, halo-C₂-C₆-alkenylsulfinyl, C₂-C₆-alkenylsulfonyl, halo-C₂-C₆-alkenylsulfonyl, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkylsulfonylamino, halo-C₁-C₆-alkylsulfonylamino, C₁-C₆-alkylcarbonyl, halo-C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl; unsubstituted phenyl or phenyl which is substituted once or many times, whereby the substituents may be independent of one another and are selected from the group comprising halogen, nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, halo-C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl and halo-C₁-C₆-alkylsulfonyl; unsubstituted phenoxy or phenoxy which is substituted once or many times, whereby the substituents may be independent of one another and are selected from the group comprising halogen, nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, halo-C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl and halo-C₁-C₆-alkylsulfonyl; unsubstituted phenylacetylenyl or phenylacetylenyl which is substituted once or many times, whereby the substituents may be independent of one another and are selected from the group comprising halogen, nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, halo-C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl and halo-C₁-C₆-alkylsulfonyl; and unsubstituted pyridyloxy or pyridyloxy which is substituted once or many times, whereby the substituents may be independent of one another and are selected from the group comprising halogen, nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, halo-C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl and halo-C₁-C₆-alkylsulfonyl; unsubstituted heteroaryl or heteroaryl which is substituted once or many times, whereby the substituents may be independent of one another and are selected from the group comprising halogen, nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, halo-C₂-C₆-alkenyloxy, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, halo-C₁-C₆-alkylsulfinyl, C₂-C₆-alkenylthio, halo-C₂-C₆-alkenylthio, C₂-C₆-alkenylsulfinyl, halo-C₂-C₆-alkenylsulfinyl, C₁-C₆-alkylsulfonyl and halo-C₁-C₆-alkylsulfonyl, C₂-C₆-alkenylsulfonyl, halo-C₂-C₆-alkenylsulfonyl, C₁-C₆-alkylamino and di-C₁-C₆-alkylamino; or unsubstituted naphthyl or quinolyl, or naphthyl or quinolyl which is substituted once or many times, whereby the substituents may be independent of one another and are selected from the group comprising halogen, nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, halo-C₂-C₆-alkenyloxy, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, halo-C₁-C₆-alkylsulfinyl, C₂-C₆-alkenylthio, halo-C₂-C₆-alkenylthio, C₂-C₆-alkenylsulfinyl, halo-C₂-C₆-alkenylsulfinyl, C₁-C₆-alkylsulfonyl and halo-C₁-C₆-alkylsulfonyl, C₂-C₆-alkenylsulfonyl, halo-C₂-C₆-alkenylsulfonyl, C₁-C₆-alkylamino and di-C₁-C₆-alkylamino; Q₁ signifies CH₂, OCH₂, S, S(O), S(O₂) or C(O); Q₂ signifies a direct bond or C(O); R₃ signifies hydrogen, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, cyano-C₁-C₆-alkyl, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio, C₂-C₆-alkenyl, C₂-C₆-alkinyl, benzyl or C₁-C₆-alkoxymethyl; R₄, R₅, R₆, R₇ and R₈ either, independently of one another, signify hydrogen, halogen, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₃-C₆-cycloalkyl that is either unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group comprising halogen and C₁-C₆-alkyl; phenyl that is either unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group comprising halogen, nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, halo-C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, halo-C₁-C₆-alkylsulfonyl, C₁-C₆-alkylamino or di-C₁-C₆-alkylamino; or R₄ and R₅ together signify C₂-C₆-alkylene; W signifies O, S, S(O₂) or N(R₉); R₉ signifies hydrogen or C₁-C₆-alkyl; a signifies 1, 2, 3 or 4; b signifies 0, 1, 2, 3 or 4; and n is 0 or 1. Alkyl—as a group per se and as structural element of other groups and compounds such as halogen-alkyl, alkylamino, alkoxy, alkylthio, alkylsulfinyl and alkylsulfonyl—is, in each case with due consideration of the specific number of carbon atoms in the group or compound in question, either straight-chained, i.e. methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl or octyl, or branched, e.g. isopropyl, isobutyl, sec.-butyl, tert.-butyl, isopentyl, neopentyl or isohexyl. Cycloalkyl—as a group per se and as structural element of other groups and compounds such as halocycloalkyl, cycloalkoxy and cycloalkylthio,—is, in each case with due consideration of the specific number of carbon atoms in the group or compound in question, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl. Alkenyl—as a group per se and as structural element of other groups and compounds—is, in each case with due consideration of the specific number of carbon atoms in the group or compound in question and of the conjugated or isolated double bonds—either straight-chained, e.g. allyl, 2-butenyl, 3-pentenyl, 1-hexenyl, 1-heptenyl, 1,3-hexadienyl or 1,3-octadienyl, or branched, e.g. isopropenyl, isobutenyl, isoprenyl, tert.-pentenyl, isohexenyl, isoheptenyl or isooctenyl. Alkinyl—as a group per se and as structural element of other groups and compounds—is, in each case with due consideration of the specific number of carbon atoms in the group or compound in question and of the conjugated or isolated double bonds—either straight-chained, e.g. propargyl, 2-butinyl, 3-pentinyl, 1-hexinyl, 1-heptinyl, 3-hexen-1-inyl or 1,5-heptadien-3-inyl, or branched, e.g. 3-methylbut-1-inyl, 4-ethylpent-1-inyl, 4-methylhex-2-inyl or 2-methylhept-3-inyl.

Heteroaryl is pyridyl, thienyl, furanyl, pyrryl, benzothienyl, benzofuranyl, indolyl or indazolyl, preferably pyridyl or thienyl, especially pyridyl.

As a rule, halogen signifies fluorine, chlorine, bromine or iodine. The same applies to halogen in combination with other significances, such as halogenalkyl or halogenphenyl.

Halogen-substituted carbon-containing groups and compounds may be partially halogenated or perhalogenated, whereby in the case of multiple halogenation, the halogen substituents may be identical or different. Examples of halogen-alkyl—as a group per se and as structural element of other groups and compounds such as halogen-alkoxy or halogen-alkylthio,—are methyl which is mono- to trisubstituted by fluorine, chlorine and/or bromine, such as CHF₂ or CF₃; ethyl which is mono- to pentasubstituted by fluorine, chlorine and/or bromine, such as CH₂CF₃, CF₂CF₃, CF₂CCl₃, CF₂CHCl₂, CF₂CHF₂, CF₂CFCl₂, CF₂CHBr₂, CF₂CHClF, CF₂CHBrF or CClFCHClF; propyl or isopropyl, mono- to heptasubstituted by fluorine, chlorine and/or bromine, such as CH₂CHBrCH₂Br, CF₂CHFCF₃, CH₂CF₂CF₃ or CH(CF₃)₂; butyl or one of its isomers, mono- to nonasubstituted by fluorine, chlorine and/or bromine, such as CF(CF₃)CHFCF₃ or CH₂(CF₂)₂CF₃; pentyl or one of its isomers substituted one to eleven times by fluorine, chlorine and/or bromine, such as CF(CF₃)(CHF)₂CF₃ or CH₂(CF₂)₃CF₃; and hexyl or one of its isomers substituted one to thirteen times by fluorine, chlorine and/or bromine, such as (CH₂)₄CHBrCH₂Br, CF₂(CHF)₄CF₃, CH₂(CF₂)₄CF₃ or C(CF₃)₂(CHF)₂CF₃.

Alkoxy groups preferably have a chain length of 1 to 6 carbon atoms. Alkoxy is for example methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, sec.-butoxy and tert.-butoxy, as well as the isomers pentyloxy and hexyloxy; preferably methoxy and ethoxy. Halogenalkoxy groups preferably have a chain length of 1 to 6 carbon atoms. Halogenalkoxy is e.g. fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2-difluoroethoxy and 2,2,2-trichloroethoxy; preferably difluoromethoxy, 2-chloroethoxy and trifluoromethoxy.

Preferred embodiments within the scope of the invention are:

(1) A compound of formula I, wherein Ar₁ and Ar₂, independently of one another, signify unsubstituted phenyl or phenyl which is substituted once or many times, whereby the substituents may be independent of one another and are selected from the group comprising halogen, nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₂-C₆-alkenyl, halo-C₂-C₆-alkenyl, C₂-C₆-alkinyl, C₃-C₆-cycloalkyl, C₂-C₆-alkenyloxy, halo-C₂-C₆-alkenyloxy, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio, C₁-C₆-alkylsulfonyloxy, halo-C₁-C₆-alkylsulfonyloxy, C₁-C₆-alkylsulfinyl, halo-C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, halo-C₁-C₆-alkylsulfonyl, C₂-C₆-alkenylthio, halo-C₂-C₆-alkenylthio, C₂-C₆-alkenylsulfinyl, halo-C₂-C₆-alkenylsulfinyl, C₂-C₆-alkenylsulfonyl, halo-C₂-C₆-alkenylsulfonyl, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkylsulfonylamino, halo-C₁-C₆-alkylsulfonylamino, C₁-C₆-alkylcarbonyl, halo-C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl; unsubstituted phenyl or phenyl which is substituted once or many times, whereby the substituents may be independent of one another and are selected from the group comprising halogen, nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, halo-C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl and halo-C₁-C₆-alkylsulfonyl; unsubstituted phenoxy or phenoxy which is substituted once or many times, whereby the substituents may be independent of one another and are selected from the group comprising halogen, nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, halo-C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl and halo-C₁-C₆-alkylsulfonyl; unsubstituted phenylacetylenyl or phenylacetylenyl which is substituted once or many times, whereby the substituents may be independent of one another and are selected from the group comprising halogen, nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, halo-C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl and halo-C₁-C₆-alkylsulfonyl; and unsubstituted pyridyloxy or pyridyloxy which is substituted once or many times, whereby the substituents may be independent of one another and are selected from the group comprising halogen, nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, halo-C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl and halo-C₁-C₆-alkylsulfonyl; unsubstituted heteroaryl or heteroaryl which is substituted once or many times, whereby the substituents may be independent of one another and are selected from the group comprising halogen, nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, halo-C₂-C₆-alkenyloxy, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, halo-C₁-C₆-alkylsulfinyl, C₂-C₆-alkenylthio, halo-C₂-C₆-alkenylthio, C₂-C₆-alkenylsulfinyl, halo-C₂-C₆-alkenylsulfinyl, C₁-C₆-alkylsulfonyl and halo-C₁-C₆-alkylsulfonyl, C₂-C₆-alkenylsulfonyl, halo-C₂-C₆-alkenylsulfonyl, C₁-C₆-alkylamino and di-C₁-C₆-alkylamino; or unsubstituted naphthyl or quinolyl, or naphthyl or quinolyl which is substituted once or many times, whereby the substituents may be Independent of one another and are selected from the group comprising halogen, nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, halo-C₂-C₆-alkenyloxy, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, halo-C₁-C₆-alkylsulfinyl, C₂-C₆-alkenylthio, halo-C₂-C₆-alkenylthio, C₂-C₆-alkenylsulfinyl, halo-C₂-C₆-alkenylsulfinyl, C₁-C₆-alkylsulfonyl and halo-C₁-C₆-alkylsulfonyl, C₂-C₆-alkenylsulfonyl, halo-C₂-C₆-alkenylsulfonyl, C₁-C₆-alkylamino and di-C₁-C₆-alkylamino; Q₁ signifies CH₂, OCH₂, S, S(O), S(O₂) or C(O); Q₂ signifies a direct bond or C(O); R₃ signifies hydrogen, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, cyano-C₁-C₆-alkyl, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio, C₂-C₆-alkenyl or C₂-C₆-alkinyl; R₄, R₅, R₆, R₇ and R₈ either, independently of one another, signify hydrogen, halogen, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₃-C₆-cycloalkyl that is either unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group comprising halogen and C₁-C₆-alkyl; phenyl that is either unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group comprising halogen, nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, halo-C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, halo-C₁-C₆-alkylsulfonyl, C₁-C₆-alkylamino or di-C₁-C₆-alkylamino; or R₄ and R₅ together signify C₂-C₆-alkylene; W signifies O, S, S(O₂) or N(R₉); R₉ signifies hydrogen or C₁-C₆-alkyl; a signifies 1, 2, 3 or 4; b signifies 0, 1, 2, 3 or 4; and n is 0 or 1; (2) A compound of formula I, wherein Ar₁ and Ar₂, independently of one another, signify unsubstituted phenyl or phenyl which is substituted once or many times, whereby the substituents may be independent of one another and are selected from the group comprising halogen, nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₂-C₆-alkenyl, halo-C₂-C₆-alkenyl, C₂-C₆-alkinyl, C₃-C₆-cycloalkyl, C₂-C₆-alkenyloxy, halo-C₂-C₆-alkenyloxy, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkylcarbonyl, halo-C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylaminocarbonyl and di-C₁-C₆-alkylaminocarbonyl; heteroaryl that is either unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group comprising halogen, nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, halo-C₂-C₆-alkenyloxy, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio, C₁-C₆-alkylamino and di-C₁-C₆-alkylamino; or naphthyl that is either unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group comprising halogen, nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, halo-C₂-C₆-alkenyloxy, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio, C₁-C₆-alkylamino and di-C₁-C₆-alkylamino; especially phenyl that is, independently of one another, either unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group comprising halogen, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio, C₁-C₆-alkylcarbonyl, halo-C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylaminocarbonyl and di-C₁-C₆-alkylaminocarbonyl; heteroaryl that is either unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group comprising halogen, C₁-C₆-alkyl, halo-C₁₋₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₁-C₆-alkylamino and di-C₁-C₆-alkylamino; or naphthyl that is either unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group comprising halogen, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₁-C₆-alkylamino and di-C₁-C₆-alkylamino; most particularly phenyl that is, independently of one another, either unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group comprising halogen, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy and halo-C₁-C₆-alkoxy; or heteroaryl that is either unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group comprising halogen, C₁-C₆-alkyl and halo-C₁-C₆-alkyl; (3) A compound of formula I, wherein Q₁ is CH₂, S, S(O₂) or C(O); especially C(O); (4) A compound of formula I, wherein R₃ signifies hydrogen, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, cyano-C₁-C₆-alkyl, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio, C₂-C₆-alkenyl or C₂-C₆-alkinyl; especially hydrogen or C₁-C₆-alkyl; most particularly hydrogen; (5) A compound of formula I, wherein R₄, R₅, R₆, R₇ and R₈, independently of one another, are hydrogen, halogen, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₃-C₆-Cycloalkyl; phenyl that is either unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group comprising halogen, nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy and halo-C₁-C₆-alkoxy; especially, independently of one another, hydrogen, halogen, C₁-C₆-alkyl, halo-C₁-C₆-alkyl or C₃-C₆-cycloalkyl; especially, independently of one another, hydrogen, halogen, C₁-C₆-alkyl or halo-C₁-C₆-alkyl; (6) A compound of formula I, wherein W is O, S or N(R₉); especially O or N(R₉); particularly O; (7) A compound of formula I, wherein R₉ signifies hydrogen or C₁—R₄-alkyl; especially hydrogen or C₁-C₂-alkyl; particularly methyl; (8) A compound of formula I, wherein a is 1, 2 or 4; especially 1 or 4; particularly 1; (9) A compound of formula I, wherein b is 0, 1, 2 or 4; especially 0, 1 or 4; particularly 0 or 1; (10) A compound of formula I, wherein n is 0; (11) A compound of formula I, wherein Ar₁ and Ar₂, independently of one another, signify unsubstituted phenyl or phenyl which is substituted once or many times, whereby the substituents may be independent of one another and are selected from the group comprising halogen, nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₂-C₆-alkenyl, halo-C₂-C₆-alkenyl, C₂-C₆-alkinyl, C₃-C₆-cycloalkyl, C₂-C₆-alkenyloxy, halo-C₂-C₆-alkenyloxy, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkylcarbonyl, halo-C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylaminocarbonyl and di-C₁-C₆-alkylaminocarbonyl; heteroaryl that is either unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group comprising halogen, nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, halo-C₂-C₆-alkenyloxy, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio, C₁-C₆-alkylamino and di-C₁-C₆-alkylamino; or naphthyl that is either unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group comprising halogen, nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, halo-C₂-C₆-alkenyloxy, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio, C₁-C₆-alkylamino and di-C₁-C₆-alkylamino; Q₁ signifies CH₂, S, S(O₂) or C(O); R₃ signifies hydrogen or C₁-C₆-alkyl; R₄, R₅, R₆, R₇ and R₈, independently of one another, are hydrogen, halogen, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₃-C₆-Cycloalkyl; phenyl that is either unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group comprising halogen, nitro, cyano, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy and halo-C₁-C₆-alkoxy; W signifies O, S or N(R₉); R₉ signifies hydrogen or C₁-C₄-alkyl; a signifies 1, 2 or 4; b signifies 0, 1, 2 or 4; and n signifies 0; (12) A compound of formula I, wherein Ar₁ and Ar₂, independently of one another, signify phenyl that is either unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group comprising halogen, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio, C₁-C₆-alkylcarbonyl, halo-C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylaminocarbonyl and di-C₁-C₆-alkylaminocarbonyl; Q₁ signifies C(O); R₃ signifies hydrogen or C₁-C₂-alkyl; R₄, R₅, R₆, R₇ and R₈, independently of one another, signify hydrogen, halogen, C₁-C₆-alkyl, halo-C₁-C₆-alkyl or C₃-C₆-cycloalkyl; W signifies O or N(R₉); R₉ signifies hydrogen or C₁-C₂-alkyl; a signifies 1 or 4; b signifies 0, 1 or 4; and n signifies 0; (13) A compound of formula I, wherein Ar₁ and Ar₂, independently of one another, signify phenyl that is either unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group comprising halogen, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy and halo-C₁-C₆-alkoxy; or heteroaryl that is either unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and are selected from the group comprising halogen, C₁-C₆-alkyl and halo-C₁-C₆-alkyl; Q₁ signifies C(O); R₃ signifies hydrogen; R₄, R₅, R₆, R₇ and R₈, independently of one another, signify hydrogen, halogen, C₁-C₆-alkyl or halo-C₁-C₆-alkyl; W signifies O; R₉ signifies methyl; a signifies 1; b signifies 0 or 1; and n is O.

Within the context of the invention, particular preference is given to the compounds of formula I listed in Table 1, and most particularly those named in the synthesis examples.

A further object of the invention is the process for the preparation of the compounds of formula I, respectively in free form or in salt form, for example characterised in that a compound of formula

which is known or may be produced analogously to corresponding known compounds, and wherein R₃, R₄, R₅, R₆, R₇, R₈, W, Ar₂, a and b are defined as given for formula I, is reacted with a compound of formula

which is known or may be prepared analogously to corresponding known compounds, and wherein Ar₁, Q₁, Q₂ and n are defined as given for formula I and X is a leaving group, optionally in the presence of a basic catalyst, and if desired, a compound of formula I obtained according to the method or in another way, respectively in free form or in salt form, is converted into another compound of formula I, a mixture of isomers which is obtainable by this process is separated and the desired isomer isolated and/or a free compound of formula I obtained according to the method is converted into a salt or a salt of a compound of formula I obtained according to the method is converted into the free compound of formula I or into another salt.

What has been stated above for salts of compounds I also applies analogously to salts of the starting materials listed hereinabove and hereinbelow.

The reaction partners can be reacted with one another as they are, i.e. without the addition of a solvent or diluent, e.g. in the melt. In most cases, however, the addition of an inert solvent or diluent, or a mixture thereof, is of advantage. Examples of such solvents or diluents are: aromatic, aliphatic and alicyclic hydrocarbons and halogenated hydrocarbons, such as benzene, toluene, xylene, mesitylene, tetraline, chlorobenzene, dichlorobenzene, bromobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, trichloromethane, tetrachloromethane, dichloroethane, trichloroethene or tetrachloroethene; ethers, such as diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, tert-butyl methyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol dimethylether, dimethoxydiethylether, tetrahydrofuran or dioxane; ketones such as acetone, methyl ethyl ketone or methyl isobutyl ketone; amides such as N,N-dimethylformamide, N,N-diethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone or hexamethylphosphoric acid triamide; nitriles such as acetonitrile or propionitrile; and sulfoxides, such as dimethyl sulfoxide.

Preferred leaving groups are OH, halogens, tosylates, mesylates and triflates, most preferably halogens, especially chlorine.

Suitable bases for facilitating the reaction are e.g. alkali metal or alkaline earth metal hydroxides, hydrides, amides, alkanolates, acetates, carbonates, dialkylamides or alkylsilylamides; alkylamines, alkylenediamines, optionally N-alkylated, optionally unsaturated, cycloalkylamines, basic heterocycles, ammonium hydroxides, as well as carbocyclic amines. Those which may be mentioned by way of example are sodium hydroxide, hydride, amide, methanolate, acetate, carbonate, potassium tert.-butanolate, hydroxide, carbonate, hydride, lithium diisopropylamide, potassium bis(trimethylsilyl)-amide, calcium hydride, triethylamine, diisopropylethylamine, triethylenediamine, cyclohexylamine, N-cyclohexyl-N,N-dimethylamine, N,N-diethylaniline, pyridine, 4-(N,N-dimethylamino)pyridine, quinuclidine, N-methylmorpholine, benzyltrimethylammonium hydroxide, as well as 1,5-diazabicyclo[5.4.0]undec-5-ene (DBU).

The reaction advantageously takes place in a temperature range of ca. 0° C. to ca. 150° C., preferably from ca. 20° C. to ca. 100° C.

Salts of compounds I may be produced in known manner. Acid addition salts, for example, are obtainable from compounds I by treating with a suitable acid or a suitable ion exchange reagent, and salts with bases are obtainable by treating with a suitable base or a suitable ion exchange reagent

Salts of compounds I can be converted into the free compounds I by the usual means, acid addition salts e.g. by treating with a suitable basic composition or with a suitable ion exchange reagent, and salts with bases e.g. by treating with a suitable acid or a suitable ion exchange reagent.

Salts of compounds I can be converted into other salts of compounds I in a known manner; acid addition salts can be converted for example into other acid addition salts, e.g. by treating a salt of an inorganic acid, such as a hydrochloride, with a suitable metal salt, such as a sodium, barium, or silver salt, of an acid, e.g. with silver acetate, in a suitable solvent, in which a resulting inorganic salt, e.g. silver chloride, is insoluble and thus precipitates out from the reaction mixture.

Depending on the method and/or reaction conditions, compounds I with salt-forming characteristics can be obtained in free form or in the form of salts.

Compounds I can also be obtained in the form of their hydrates and/or also can include other solvents, used for example where necessary for the crystallisation of compounds present in solid form.

The compounds I and II may be present in the form of one of the possible isomers or as a mixture thereof, depending for example on the number and the absolute and relative configuration of the asymmetric carbon atoms, as pure isomers, such as antipodes and/or diastereoisomers, or as isomeric mixtures, such as a mixture of enantiomers, for example racemates, diastereoisomeric mixtures or racemate mixtures; the invention relates both to the pure isomers and to all possible isomeric mixtures, and is hereinbefore and hereinafter understood as doing so, even if stereochemical details are not specifically mentioned in every case.

Depending on the choice of starting materials and methods, diastereoisomeric mixtures and racemate mixtures of compounds I and II, which are obtainable by the process or in another way, may be separated in known manner, on the basis of the physical-chemical differences in their components, into the pure diastereoisomers or racemates, for example by fractional crystallisation, distillation and/or chromatography.

Resolution of mixtures of enantiomers that are obtainable accordingly, such as racemates, may be achieved by known methods, for example by recrystallisation from an optically active solvent, by chromatography on chiral adsorbents, e.g. high-pressure liquid chromatography (HPLC) on acetyl cellulose, with the assistance of appropriate microorganisms, by cleavage with specific immobilised enzymes, through the formation of inclusion compounds, e.g. using chiral crown ethers, whereby only one enantiomer is complexed.

According to the invention, apart from isolation of corresponding isomer mixtures, generally known methods of diastereoselective or enantioselective synthesis can also be applied to obtain pure diastereoisomers or enantiomers, e.g. by carrying out the method of the invention using educts with correspondingly suitable stereochemistry.

It is advantageous to isolate or synthesise the biologically more active isomer, e.g. enantiomer, or isomer mixture, e.g. enantiomer mixture, provided that the individual components have differing biological efficacy.

In the method of the present invention, the starting materials and intermediates used are preferably those that lead to the compounds I described at the beginning as being especially useful.

The invention relates especially to the method of preparation described in the example.

Starting materials and intermediates, which are new and are used according to the invention for the preparation of compounds I, as well as their usage and process for the preparation thereof, similarly form an object of the invention.

The compounds I according to the invention are notable for their broad activity spectrum and are valuable active ingredients for use in pest control, including in particular the control of endo- and ecto-parasites on animals, whilst being well-tolerated by warm-blooded animals, fish and plants,

In the context of the present invention, ectoparasites are understood to be in particular insects, mites and ticks. These include insects of the order: Lepidoptera, Coleoptera, Homoptera, Heteroptera, Diptera, Thysanoptera, Orthoptera, Anoplura, Siphonaptera, Mallophaga, Thysanura, Isoptera, Psocoptera and Hymenoptera. However, the ectoparasites which may be mentioned in particular are those which trouble humans or animals and carry pathogens, for example flies such as Musca domestica, Musca vetustissima, Musca autumnalis, Fannia caniculadis, Sarcophaga carnadia, Lucilla cuprina, Hypoderma bovis, Hypoderma lineatum, Chrysomyia chloropyga, Dermatobia hominis, Cochliomyia hominivorax, Gasterophilus intestinalls, Oestrus ovis, Stomoxys calcitrans, Haematobia irritans and midges (Nematocera), such as Culicidae, Simullidae, Psychodidae, but also blood-sucking parasites, for example fleas, such as Ctenocephalides felis and Ctenocephalides canis (cat and dog fleas), Xenopsylla cheopis, Pulex irritans, Dermatophilus penetrans, lice, such as Damalina ovis, Pediculus humanis, biting flies and horse-flies (Tabanidae), Haematopota spp. such as Haematopota pluvialis, Tabanidea spp. such as Tabanus nigrovittatus, Chrysopsinae spp. such as Chrysops caecutiens, tsetse flies, such as species of Glossinia, biting insects, particularly cockroaches, such as Blatella germanica, Blatta orientalis, Periplaneta americana, mites, such as Dermanyssus gallinae, Sarcoptes scabiel, Psoroptes ovis and Psorergates spp. and last but not least ticks. The latter belong to the order Acarina. Known representatives of ticks are, for example, Boophilus, Amblyomma, Anocentor, Dermacentor, Haemaphysalis, Hyalomma, Ixodes, Rhipicentor, Margaropus, Rhipicephalus, Argas, Otobius and Ornithodoros and the like, which preferably infest warm-blooded animals including farm animals, such as cattle, pigs, sheep and goats, poultry such as chickens, turkeys and geese, fur-bearing animals such as mink, foxes, chinchillas, rabbits and the like, as well as domestic animals such as cats and dogs, but also humans.

The compounds I according to the invention are also active against all or individual development stages of animal pests showing normal sensitivity, as well as those showing resistance, such as insects and members of the order Acarina. The insecticidal, ovicidal and/or acaricidal effect of the active substances of the invention can manifest itself directly, i.e. killing the pests either immediately or after some time has elapsed, for example when moulting occurs, or by destroying their eggs, or indirectly, e.g. reducing the number of eggs laid and/or the hatching rate, good efficacy corresponding to a pesticidal rate (mortality) of at least 50 to 60%.

Compounds I can also be used against hygiene pests, especially of the order Diptera of the families Sarcophagidae, Anophilidae and Culicidae; the orders Orthoptera, Dictyoptera (e.g. the family Blattidae) and Hymenoptera (e.g. the family Formicidae).

Compounds I also have sustainable efficacy on parasitic mites and insects of plants. In the case of spider mites of the order Acarina, they are effective against eggs, nymphs and adults of Tetranychidae (Tetranychus spp. and Panonychus spp.).

They have high activity against sucking insects of the order Homoptera, especially against pests of the families Aphididae, Delphacidae, Cicadellidae, Psyllidae, Loccidae, Diaspididae and Eriophydidae (e.g. rust mite on citrus fruits); the orders Hemiptera, Heteroptera and Thysanoptera, and on the plant-eating insects of the orders Lepidoptera, Coleoptera, Diptera and Orthoptera

They are similarly suitable as a soil insecticide against pests in the soil.

The compounds of formula I are therefore effective against all stages of development of sucking insects and eating insects on crops such as cereals, cotton, rice, maize, soya, potatoes, vegetables, fruit, tobacco, hops, citrus, avocados and other crops.

The compounds of formula I are also effective against plant nematodes of the species Meloidogyne, Heterodera, Pratylenchus, Ditylenchus, Radopholus, Rizoglyphus etc.

In particular, the compounds are effective against helminths, in which the endoparasitic nematodes and trematodes may be the cause of serious diseases of mammals and poultry, e.g. sheep, pigs, goats, cattle, horses, donkeys, dogs, cats, guinea-pigs and exotic birds. Typical nematodes of this indication are: Haemonchus, Trichostrongylus, Ostertagia, Nematodirus, Coopedia, Ascaris, Bunostonum, Oesophagostonum, Charbertia, Trichuris, Strongylus, Trichonema, Dictyocaulus, Capilladia, Heterakis, Toxocara, Ascaridia, Oxyuris, Ancylostoma, Uncinaria, Toxascadis and Parascaris. The trematodes include, in particular, the family of Fasclolideae, especially Fasciola hepatica. The particular advantage of the compounds of formula I is their efficacy against those parasites that are resistant towards active ingredients based on benzimidazole.

Certain pests of the species Nematodirus, Coopeda and Oesophagostonum infest the intestinal tract of the host animal, while others of the species Haemonchus and Ostertagia are parasitic in the stomach and those of the species Dictyocaulus are parasitic in the lung tissue. Parasites of the families Filariidae and Setariidae may be found in the internal cell tissue and in the organs, e.g. the heart, the blood vessels, the lymph vessels and the subcutaneous tissue. A particularly notable parasite is the heartworm of the dog, Dirofilaria immitis. The compounds of formula I are highly effective against these parasites.

The pests which may be controlled by the compounds of formula I also include those from the class of Cestoda (tapeworms), e.g. the families Mesocestoidae, especially of the genus Mesocestoides, in particular M. lineatus; Dilepidide, especially Dipylidium caninum, Joyeuxiella spp., in particular Joyeuxiella pasquali, and Diplopylidium spp., and Taeniidae, especially Taenia pisiformis, Taenia cervi, Taenia ovis, Taneia hydatigena, Taenia multiceps, Taenia taeniaeformis, Taenla sedalis, and Echinocuccus spp., most preferably Taneia hydatigena, Taenia ovis, Taenia multiceps, Taenia serialis; Echinocuccus granulosus and Echinococcus granulosus and Echinococcus multiloculatis, as well as Multiceps multiceps.

Most particularly, Taenia hydatigena, T. pisiformis, T. ovis, T. taeniaeformis, Multiceps multiceps, Joyeuxiella pasquali, Dipylidium caninum, Mesocestoides spp., Echinococcus granulosus and E. multiloculais are controlled on or in dogs and cats simultaneously with Dirofilaria immitis, Ancylostoma ssp., Toxocara ssp. and/or Trichuris vulpis. Equally preferred, Ctenocephalides felis and/or C. canis are simultaneously controlled with the above-mentioned nematodes and cestodes.

Furthermore, the compounds of formula I are suitable for the control of human pathogenic parasites. Of these, typical representatives that appear in the digestive tract are those of the species Ancylostoma, Necator, Ascaris, Strongyloides, Trichinella, Capillaria, Trichuris and Enterobius. The compounds of the present invention are also effective against parasites of the species Wuchereria, Brugia, Onchocerca and Loa from the family of Filariidae, which appear in the blood, in the tissue and in various organs, and also against Dracunculus and parasites of the species Strongyloides and Trichinella, which infect the gastrointestinal tract in particular.

In addition, the compounds of formula I are also effective against harmful and pathogenic fungi on plants, as well as on humans and animals.

The good pesticidal activity of the compounds of formula I according to the invention corresponds to a mortality rate of at least 50-60% of the pests mentioned. In particular, the compounds of formula I are notable for the exceptionally long duration of efficacy.

The compounds of formula I are preferably employed in unmodified form or preferably together with the adjuvants conventionally used in the art of formulation and may therefore be processed in a known manner to give, for example, emulsifiable concentrates, directly dilutable solutions, dilute emulsions, soluble powders, granules or microencapsulations in polymeric substances. As with the compositions, the methods of application are selected in accordance with the intended objectives and the prevailing circumstances.

The formulation, i.e. the agents, preparations or compositions containing the active ingredient of formula I, or combinations of these active ingredients with other active ingredients, and optionally a solid or liquid adjuvant, are produced in a manner known per se, for example by intimately mixing and/or grinding the active ingredients with spreading compositions, for example with solvents, solid carriers, and optionally surface-active compounds (surfactants).

The solvents in question may be: alcohols, such as ethanol, propanol or butanol, and glycols and their ethers and esters, such as propylene glycol, dipropylene glycol ether, ethylene glycol, ethylene glycol monomethyl or -ethyl ether, ketones, such as cyclohexanone, isophorone or diacetanol alcohol, strong polar solvents, such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or dimethylformamide, or water, vegetable oils, such as rape, castor, coconut, or soybean oil, and also, if appropriate, silicone oils.

Preferred application forms for usage on warm-blooded animals in the control of helminths include solutions, emulsions, suspensions (drenches), food additives, powders, tablets including effervescent tablets, boli, capsules, micro-capsules and pour-on formulations, whereby the physiological compatibility of the formulation excipients must be taken into consideration.

The binders for tablets and boli may be chemically modified polymeric natural substances that are soluble in water or in alcohol, such as starch, cellulose or protein derivatives (e.g. methyl cellulose, carboxymethyl cellulose, ethylhydroxyethyl cellulose, proteins such as zein, gelatin and the like), as well as synthetic polymers, such as polyvinyl alcohol, polyvinyl pyrrolidone etc. The tablets also contain fillers (e.g. starch, microcrystalline cellulose, sugar, lactose etc.), glidants and disintegrants.

If the anthelminthics are present in the form of feed concentrates, then the carriers used are e.g. performance feeds, feed grain or protein concentrates. Such feed concentrates or compositions may contain, apart from the active ingredients, also additives, vitamins, antibiotics, chemotherapeutics or other pesticides, primarily bacteriostats, fungistats, coccidiostats, or even hormone preparations, substances having anabolic action or substances which promote growth, which affect the quality of meat of animals for slaughter or which are beneficial to the organism in another way. If the compositions or the active ingredients of formula I contained therein are added directly to feed or to the drinking troughs, then the formulated feed or drink contains the active ingredients preferably in a concentration of ca. 0.0005 to 0.02.% by weight (5-200 ppm).

The compounds of formula I according to the invention may be used alone or in combination with other biocides. They may be combined with pesticides having the same sphere of activity e.g. to increase activity, or with substances having another sphere of activity e.g. to broaden the range of activity. It can also be sensible to add so-called repellents. If the range of activity is to be extended to endoparasites, e.g. wormers, the compounds of formula I are suitably combined with substances having endoparasitic properties. Of course, they can also be used in combination with antibacterial compositions. Since the compounds of formula I are adulticides, i.e. since they are effective in particular against the adult stage of the target parasites, the addition of pesticides which instead attack the juvenile stages of the parasites may be very advantageous. In this way, the greatest part of those parasites that produce great economic damage will be covered. Moreover, this action will contribute substantially to avoiding the formation of resistance. Many combinations may also lead to synergistic effects, i.e. the total amount of active ingredient can be reduced, which is desirable from an ecological point of view. Preferred groups of combination partners and especially preferred combination partners are named in the following, whereby combinations may contain one or more of these partners in addition to a compound of formula I.

Suitable partners in the mixture may be biocides, e.g. the insecticides and acaricides with a varying mechanism of activity, which are named in the following and have been known to the person skilled in the art for a long time, e.g. chitin synthesis inhibitors, growth regulators; active ingredients which act as juvenile hormones; active ingredients which act as adulticides; broad-band insecticides, broad-band acaricides and nematicides; and also the well known anthelminthics and insect- and/or acarid-deterring substances, said repellents or detachers.

Non-limitative examples of suitable insecticides and acaricides are:

1. Abamectin 2. AC 303 630 3. Acephat 4. Acrinathrin 5. Alanycarb 6. Aldicarb 7. α-Cypermethrin 8. Alphamethrin 9. Amitraz 10. Avermectin B₁ 11. AZ 60541 12. Azinphos A 13. Azinphos M 14. Azinphos-methyl 15. Azocyclotin 16. Bacillus subtil. toxin 17. Bendiocarb 18. Benfuracarb 19. Bensultap 20. β-Cyfluthrin 21. Bifenthrin 22. BPMC 23. Brofenprox 24. Bromophos A 25. Bufencarb 26. Buprofezin 27. Butocarboxin 28. Butylpyridaben 29. Cadusafos 30. Carbaryl 31. Carbofuran 32. Carbophenthion 33. Cartap 34. Chloethocarb 35. Chlorethoxyfos 36. Chlorfenapyr 37. Chlorfluazuron 38. Chlormephos 39. Chlorpyrifos 40. Cis-Resmethrin 41. Clocythrin 42. Clofentezin 43. Cyanophos 44. Cycloprothrin 45. Cyfluthrin 46. Cyhexatin 47. D 2341 48. Deltamethrin 49. Demeton M 50. Demeton S 51. Demeton-S-methyl 52. Dibutylaminothio 53. Dichlofenthion 54. Dicliphos 55. Diethion 56. Diflubenzuron 57. Dimethoat 58. Dimethylvinphos 59. Dioxathion 60. DPX-MP062 61. Edifenphos 62. Emamectin 63. Endosulfan 64. Esfenvalerat 65. Ethiofencarb 66. Ethion 67. Ethofenprox 68. Ethoprophos 69. Etrimphos 70. Fenamiphos 71. Fenazaquin 72. Fenbutatinoxid 73. Fenitrothion 74. Fenobucarb 75. Fenothiocarb 76. Fenoxycarb 77. Fenpropathrin 78. Fenpyrad 79. Fenpyroximate 80. Fenthion 81. Fenvalerate 82. Fipronil 83. Fluazinam 84. Fluazuron 85. Flucycloxuron 86. Flucythrinat 87. Flufenoxuron 88. Flufenprox 89. Fonophos 90. Formothion 91. Fosthiazat 92. Fubfenprox 93. HCH 94. Heptenophos 95. Hexaflumuron 96. Hexythiazox 97. Hydroprene 98. Imidacloprid 99. insect-active fungi 100. insect-active nematodes 101. insect-active viruses 102. Iprobenfos 103. Isofenphos 104. Isoprocarb 105. Isoxathion 106. Ivermectin 107. λ-Cyhalothrin 108. Lufenuron 109. Malathion 110. Mecarbam 111. Mesulfenphos 112. Metaldehyd 113. Methamidophos 114. Methiocarb 115. Methomyl 116. Methoprene 117. Metolcarb 118. Mevinphos 119. Milbemectin 120. Moxidectin 121. Naled 122. NC 184 123. NI-25, Acetamiprid 124. Nitenpyram 125. Omethoat 126. Oxamyl 127. Oxydemethon M 128. Oxydeprofos 129. Parathion 130. Parathion-methyl 131. Permethrin 132. Phenthoat 133. Phorat 134. Phosalone 135. Phosmet 136. Phoxim 137. Pirimicarb 138. Pirimiphos A 139. Pirimiphos M 140. Promecarb 141. Propaphos 142. Propoxur 143. Prothiofos 144. Prothoat 145. Pyrachlophos 146. Pyradaphenthion 147. Pyresmethrin 148. Pyrethrum 149. Pyridaben 150. Pyrimidifen 151. Pyriproxyfen 152. RH 5992 153. RH-2485 154. Salithion 155. Sebufos 156. Silafluofen 157. Spinosad 158. Sulfotep 159. Sulprofos 160. Tebufenozide 161. Tebufenpyrad 162. Tebupirimphos 163. Teflubenzuron 164. Tefluthrin 165. Temephos 166. Terbam 167. Terbufos 168. Tetrachlorvinphos 169. Thiafenox 170. Thiodicarb 171. Thiofanox 172. Thionazin 173. Thuringiensin 174. Tralomethrin 175. Triarthen 176. Triazamate 177. Triazophos 178. Triazuron 179. Trichlorfon 180. Triflumuron 181. Trimethacarb 182. Vamidothion 183. XMC (3,5,-Xylyl- methylcarbamate) 184. Xylylcarb 185. YI 5301/5302 186. ζ-Cypermethrin 187. Zetamethrin

Non-limitative examples of suitable anthelminthics are named in the following, a few representatives have insecticidal and acaricidal activity in addition to the anthelminthic activity, and are partly already in the above list.

-   (A1)     Praziquantel=2-cyclohexylcarbonyl-4-oxo-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-α]isoquinoline -   (A2)     Closantel=3,5-diiodo-N-[5-chloro-2-methyl-4-(α-cyano-4-chlorobenzyl)phenyl]-salicylamide -   (A3)     Triclabendazole=5-chloro-6-(2,3-dichlorophenoxy)-2-methylthio-1H-benzimidazole -   (A4)     Levamisol=L-(−)-2,3,5,6-tetrahydro-6-phenylimidazo[2,1b]thiazole -   (A5) Mebendazole=(5-benzoyl-1H-benzimidazol-2-yl)carbaminic acid     methylester -   (A6) Omphalotin=a macrocyclic fermentation product of the fungus     Omphalotus olearius described In WO 97/20857 -   (A7) Abamectin=avermectin B1 -   (A8) Ivermectin=22,23-dihydroavermectin B1 -   (A9)     Moxidectin=5-O-demethyl-28-deoxy-25-(1,3-dimethyl-1-butenyl)-6,28-epoxy-23-(methoxyimino)-milbemycin     B -   (A10)     Doramectin=25-cyclohexyl-5-O-demethyl-25-de(1-methylpropyl)-avermectin     A1a -   (A11) Milbemectin=mixture of milbemycin A3 and milbemycin A4 -   (A12) Milbemycinoxim=5-oxime of milbemectin

Non-limitative examples of suitable repellents and detachers are:

-   (R₁) DEET (N,N-diethyl-m-toluamide) -   (R₂) KBR 3023 N-butyl-2-oxycarbonyl-(2-hydroxy)-piperidine -   (R₃)     Cymiazole=N,-2,3-dihydro-3-methyl-1,3-thiazol-2-ylidene-2,4-xylidene

The said partners in the mixture are best known to specialists in this field. Most are described in various editions of the Pesticide Manual, The British Crop Protection Council, London, and others in the various editions of The Merck Index, Merck & Co., Inc., Rahway, N.J., USA or in patent literature. Therefore, the following listing is restricted to a few places where they may be found by way of example.

-   (I) 2-Methyl-2-(methylthio)propionaldehyde-O-methylcarbamoyloxime     (Aldicarb), from The Pesticide Manual, 11^(th) Ed. (1997), The     British Crop Protection Council, London, page 26; -   (II)     S-(3,4-dihydro-4-oxobenzo[d]-[1,2,3]-triazin-3-ylmethyl)O,O-dimethyl-phosphorodithioate     (Azinphos-methyl), from The Pesticide Manual, 11^(th)Ed. (1997), The     British Crop Protection Council, London, page 67; -   (III)     Ethyl-N-[2,3-dihydro-2,2-dimethylbenzofuran-7-yloxycarbonyl-(methyl)aminothio]-N-isopropyl-β-alaninate     (Benfuracarb), from The Pesticide Manual, 11^(th)Ed. (1997), The     British Crop Protection Council, London, page 96; -   (IV)     2-Methylbiphenyl-3-ylmethyl-(Z)-(1RS)-cis-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate     (Bifenthrin), from The Pesticide Manual, 11^(th)Ed. (1997), The     British Crop Protection Council, London, page 118; -   (V) 2-tert-butylimino-3-isopropyl-5-phenyl-1,3,5-thiadiazian-4-one     (Buprofezin), from The Pesticide Manual, 11^(th)Ed. (1997), The     British Crop Protection Council, London, page 157; -   (VI) 2,3-Dihydro-2,2-dimethylbenzofuran-7-yl-methylcarbamate     (Carbofuran), from The Pesticide Manual, 11^(th)Ed. (1997), The     British Crop Protection Council, London, page 186; -   (VII)     2,3-Dihydro-2,2-dimethylbenzofuran-7-yl-(dibutylaminothio)methylcarbamate     (Carbosulfan), from The Pesticide Manual, 11^(th)Ed. (1997), The     British Crop Protection Council, London, page 188; -   (VIII) S,S′-(2-dimethylaminotrimethylene)-bis(thiocarbamate)     (Cartap), from The Pesticide Manual, 11^(th)Ed. (1997), The British     Crop Protection Council, London, page 193; -   (IX)     1-[3,5-Dichloro-4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenyl]-3-(2,6-difluorobenzoyl)-urea     (Chlorfluazuron), from The Pesticide Manual, 11^(th)Ed. (1997), The     British Crop Protection Council, London, page 213; -   (X) O,O-diethyl-O-3,5,6-trichloro-2-pyridyl-phosphorothioate     (Chlorpyrifos), from The Pesticide Manual, 11^(th)Ed. (1997), The     British Crop Protection Council, London, page 235; -   (XI)     (RS)-α-cyano-4-fluoro-3-phenoxybenzyl-(1RS,3RS;1RS,3RS)-3-(2,2-dichlorovinyl)-2,2-di-methylcyclopropanecarboxylate     (Cyfluthrin), from The Pesticide Manual, 11^(th)Ed. (1997), The     British Crop Protection Council, London, page 293; -   (XII) Mixture of     (S)-α-cyano-3-phenoxybenzyl-(Z)-(1R,3R)-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate     and     (R)-α-cyano-3-phenoxybenzyl-(Z)-(1R,3R)-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate     (Lambda-Cyhalothrin), from The Pesticide Manual, 11^(th)Ed. (1997),     The British Crop Protection Council, London, page 300; -   (XIII) Racemate consisting of     (S)-α-cyano-3-phenoxybenzyl-(2)-(1R,3R)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate     and     (R)-α-cyano-3-phenoxybenzyl-(1S,3S)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate     (Alpha-cypermethrin), from The Pesticide Manual, 11^(th)Ed. (1997),     The British Crop Protection Council, London, page 308; -   (XIV) a mixture of the stereoisomers of (S)-α-cyano-3-phenoxybenzyl     (1RS,3RS,1     RS,3RS)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate     (zeta-Cypermethrin), from The Pesticide Manual, 11^(th)Ed. (1997),     The British Crop Protection Council, London, page 314; -   (XV)     (S)-α-cyano-3-phenoxybenzyl-(1R,3R)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate     (Deltamethrin), from The Pesticide Manual, 11^(th)Ed. (1997), The     British Crop Protection Council, London, page 344; -   (XVI) (4-chlorophenyl)-3-(2,6-difluorobenzoyl)urea (Diflubenzuron),     from The Pesticide Manual, 11^(th)Ed. (1997), The British Crop     Protection Council, London, page 395; -   (XVII)     (1,4,5,6,7,7-Hexachloro-8,9,10-trinorborn-5-en-2,3-ylenebismethylene)-sulphite     (Endosulfan), from The Pesticide Manual, 11^(th)Ed. (1997), The     British Crop Protection Council, London, page 459; -   (XVIII) α-ethylthio-o-tolyl-methylcarbamate (Ethiofencarb), from The     Pesticide Manual, 11^(th)Ed. (1997), The British Crop Protection     Council, London, page 479; -   (XIX) O,O-dimethyl-O-4-nitro-m-tolyl-phosphorothioate     (Fenitrothion), from The Pesticide Manual, 11^(th)Ed. (1997), The     British Crop Protection Council, London, page 514; -   (XX) 2-sec-butylphenyl-methylcarbamate (Fenobucarb), from The     Pesticide Manual, 11^(th)Ed. (1997), The British Crop Protection     Council, London, page 516; -   (XXI)     (RS)-α-cyano-3-phenoxybenzyl-(RS)-2-(4-chlorophenyl)-3-methylbutyrate     (Fenvalerate), from The Pesticide Manual, 11^(th)Ed. (1997), The     British Crop Protection Council, London, page 539; -   (XXII)     S-[formyl(methyl)carbamoylmethyl]-O,O-dimethyl-phosphorodithioate     (Formothion), from The Pesticide Manual, 11^(th)Ed. (1997), The     British Crop Protection Council, London, page 625; -   (XXIII) 4-Methylthio-3,5-xylyl-methylcarbamate (Methiocarb), from     The Pesticide Manual, 11^(th)Ed. (1997), The British Crop Protection     Council, London, page 813; -   (XXIV) 7-Chlorobicyclo[3.2.0]hepta-2,6-dien-6-yl-dimethylphosphate     (Heptenophos), from The Pesticide Manual, 11^(th)Ed. (1997), The     British Crop Protection Council, London, page 670; -   (XXV) 1-(6-chloro-3-pyridylmethyl)-N-nitroimidazolidin-2-ylidenamine     (Imidacloprid), from The Pesticide Manual, 11^(th)Ed. (1997), The     British Crop Protection Council, London, page 706; -   (XXVI) 2-isopropylphenyl-methylcarbamate (Isoprocarb), from The     Pesticide Manual, 11^(th)Ed. (1997), The British Crop Protection     Council, London, page 729; -   (XXVII) O,S-dimethyl-phosphoramidothioate (Methamidophos), from The     Pesticide Manual, 11^(th)Ed. (1997), The British Crop Protection     Council, London, page 808; -   (XXVIII) S-Methyl-N-(methylcarbamoyloxy)thioacetimidate (Methomyl),     from The Pesticide Manual, 11^(th)Ed. (1997), The British Crop     Protection Council, London, page 815; -   (XXIX) Methyl-3-(dimethoxyphosphinoyloxy)but-2-enoate (Mevinphos),     from The Pesticide Manual, 11^(th)Ed. (1997), The British Crop     Protection Council, London, page 844; -   (XXX) O,O-diethyl-O-4-nitrophenyl-phosphorothioate (Parathion), from     The Pesticide Manual, 11^(th)Ed. (1997), The British Crop Protection     Council, London, page 926; -   (XXXI) O,O-dimethyl-O-4-nitrophenyl-phosphorothioate     (Parathion-methyl), from The Pesticide Manual, 11^(th)Ed. (1997),     The British Crop Protection Council, London, page 928; -   (XXXII)     S-6-chloro-2,3-dihydro-2-oxo-1,3-benzoxazol-3-ylmethyl-O,O-diethyl-phosphordithioate     (Phosalone), from The Pesticide Manual, 11^(th)Ed. (1997), The     British Crop Protection Council, London, page 963; -   (XXXIII)     2-Dimethylamino-5,6-dimethylpyrimidin-4-yl-dimethylcarbamate     (Pirimicarb), from The Pesticide Manual, 11^(th)Ed. (1997), The     British Crop Protection Council, London, page 985; -   (XXXIV) 2-isopropoxyphenyl-methylcarbamate (Propoxur), from The     Pesticide Manual, 11^(th)Ed. (1997), The British Crop Protection     Council, London, page 1036; -   (XXXV)     1-(3,5-dichloro-2,4-difluorophenyl)-3-(2,6-difluorobenzoyl)urea     (Teflubenzuron), from The Pesticide Manual, 11^(th)Ed. (1997), The     British Crop Protection Council, London, page 1158; -   (XXXVI) S-tert-butylthiomethyl-O,O-dimethyl-phosphorodithioate     (Terbufos), from The Pesticide Manual, 11^(th)Ed. (1997), The     British Crop Protection Council, London, page 1165; -   (XXXVII)     ethyl-(3-tert.-butyl-1-dimethylcarbamoyl-1H-1,2,4-triazol-5-yl-thio)-acetate,     (Triazamate), from The Pesticide Manual, 11^(th)Ed. (1997), The     British Crop Protection Council, London, page 1224; -   (XXXVIII) Abamectin, from The Pesticide Manual, 11^(th)Ed. (1997),     The British Crop Protection Council, London, page 3; -   (XXXIX) 2-sec-butylphenyl-methylcarbamate (Fenobucarb), from The     Pesticide Manual, 11^(th)Ed. (1997), The British Crop Protection     Council, London, page 516; -   (XL) N-tert.-butyl-N′-(4-ethylbenzoyl)-3,5-dimethylbenzohydrazide     (Tebufenozide), from The Pesticide Manual, 11^(th)Ed. (1997), The     British Crop Protection Council, London, page 1147; -   (XLI)     (±)-5-amino-1-(2,6-dichloro-α,α,α-trifluoro-p-tolyl)-4-trifluoromethyl-sulphinylpyrazol-3-carbonitrile     (Fipronil), from The Pesticide Manual, 11^(th)Ed. (1997), The     British Crop Protection Council, London, page 545; -   (XLII) (RS)-α-cyano-4-fluoro-3-phenoxybenzyl(1RS,3RS;1     RS,3RS)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate     (beta-Cyfluthrin), from The Pesticide Manual, 11^(th)Ed. (1997), The     British Crop Protection Council, London, page 295; -   (XLIII)     (4-ethoxyphenyl)-[3-(4-fluoro-3-phenoxyphenyl)propyl](dimethyl)silane     (Silafluofen), from The Pesticide Manual, 11^(th)Ed. (1997), The     British Crop Protection Council, London, page 1105; -   (XLIV) tert.-butyl     (E)-α-(1,3-dimethyl-5-phenoxypyrazol-4-yl-methylenamino-oxy)-p-toluate     (Fenpyroximate), from The Pesticide Manual, 11^(th)Ed. (1997), The     British Crop Protection Council, London, page 530; -   (XLV)     2-tert.-butyl-5-(4-tert.-butylbenzylthio)-4-chloropyridazin-3(2H)-one     (Pyridaben), from The Pesticide Manual, 11^(th)Ed. (1997), The     British Crop Protection Council, London, page 1161; -   (XLVI) 4-[[4-(1,1-dimethylphenyl)phenyl]ethoxy]-quinazoline     (Fenazaquin), from The Pesticide Manual, 11^(th)Ed. (1997), The     British Crop Protection Council, London, page 507; -   (XLVII) 4-phenoxyphenyl-(RS)-2-(pyridyloxy)propyl-ether     (Pyriproxyfen), from The Pesticide Manual, 11^(th)Ed. (1997), The     British Crop Protection Council, London, page 1073; -   (XLVIII)     5-chloro-N-{2-[4-(2-ethoxyethyl)-2,3-dimethylphenoxy]ethyl}-6-ethylpyrimidine-4-amine     (Pyrimidifen), from The Pesticide Manual, 11^(th)Ed. (1997), The     British Crop Protection Council, London, page 1070; -   (XLIX)     (E)-N-(6-chloro-3-pyridylmethyl)-N-ethyl-N′-methyl-2-nitrovinylidenediamine     (Nitenpyram), from The Pesticide Manual, 11^(th)Ed. (1997), The     British Crop Protection Council, London, page 880; -   (L)     (E)-N¹-[(6-chloro-3-pyridyl)methyl]-N²-cyano-N¹-methylacetamidine     (NI-25, Acetamiprid), from The Pesticide Manual, 11^(th)Ed. (1997),     The British Crop Protection Council, London, page 9; -   (LI) Avermectin B₁, from The Pesticide Manual, 11^(th)Ed. (1997),     The British Crop Protection Council, London, page 3; -   (LII) an insect-active extract from a plant, especially     (2R,6aS,12aS)-1,2,6,6a,12,12a-hexhydro-2-isopropenyl-8,9-dimethoxy-chromeno[3,4-b]furo[2,3-h]chromen-6-one     (Rotenone), from The Pesticide Manual, 11^(th)Ed. (1997), The     British Crop Protection Council, London, page 1097; and an extract     from Azadirachta indica, especially azadirachtin, from The Pesticide     Manual, 11^(th)Ed. (1997), The British Crop Protection Council,     London, page 59; and -   (LII) a preparation which contains insect-active nematodes,     preferably Heterorhabditis bactedophora and Heterorhabditis megidis,     from The Pesticide Manual, 11^(th)Ed. (1997), The British Crop     Protection Council, London, page 671; Steinemema feltiae, from The     Pesticide Manual, 11^(th)Ed. (1997), The British Crop Protection     Council, London, page 1115 and Steinemema scaptedsci, from The     Pesticide Manual, 11^(th)Ed. (1997), The British Crop Protection     Council, London, page 1116; -   (LIV) a preparation obtainable from Bacillus subtilis, from The     Pesticide Manual, 11^(th)Ed. (1997), The British Crop Protection     Council, London, page 72; or from a strain of Bacillus thuringiensis     with the exception of compounds isolated from GC91 or from     NCTC11821; The Pesticide Manual, 11^(th)Ed. (1997), The British Crop     Protection Council, London, page 73; -   (LV) a preparation which contains insect-active fungi, preferably     Verticillium lecanii, from The Pesticide Manual, 11^(th) Ed. (1997),     The British Crop Protection Council, London, page 1266; Beauveda     brogniartii, from The Pesticide Manual, 11^(th)Ed. (1997), The     British Crop Protection Council, London, page 85 and Beauveda     bassiana, from The Pesticide Manual, 11^(th)Ed. (1997), The British     Crop Protection Council, London, page 83; -   (LVI) a preparation which contains insect-active viruses, preferably     Neodipridon Sertifer NPV, from The Pesticide Manual, 11^(th)Ed.     (1997), The British Crop Protection Council, London, page 1342;     Mamestra brassicae NPV, from The Pesticide Manual, 11^(th)Ed.     (1997), The British Crop Protection Council, London, page 759 and     Cydia pomonella granulosis virus, from The Pesticide Manual,     11^(th)Ed. (1997), The British Crop Protection Council, London, page     291; -   (CLXXXI)     7-chloro-2,3,4a,5-tetrahydro-2-[methoxycarbonyl(4-trifluoromethoxyphenyl)-carbamoyl]indol[1,2e]oxazoline-4a-carboxylate     (DPX-MP062, Indoxycarb), from The Pesticide Manual, 11^(th)Ed.     (1997), The British Crop Protection Council, London, page 453; -   (CLXXXII)     N′-tert.-butyl-N′-(3,5-dimethylbenzoyl)-3-methoxy-2-methylbenzohydrazide     (RH-2485, Methoxyfenozide), from The Pesticide Manual, 11^(th)Ed.     (1997), The British Crop Protection Council, London, page 1094; and -   (CLXXXIII) (N′-[4-methoxy-biphenyl-3-yl]-hydrazinecarboxylic acid     isopropylester (D 2341), from Brighton Crop Protection Conference,     1996, 487-493; -   (R₂) Book of Abstracts, 212th ACS National Meeting Orlando, Fla.,     August 25-29 (1996), AGRO-020. Publisher: American Chemical Society,     Washington, D.C. CONEN: 63BFAF.

As a consequence of the above details, a further essential aspect of the present invention relates to combination preparations for the control of parasites on warm-blooded animals, characterised in that they contain, in addition to a compound of formula I, at least one further active ingredient having the same or different sphere of activity and at least one physiologically acceptable carrier. The present invention is not restricted to two-fold combinations.

As a rule, the anthelminthic compositions according to the invention contain 0.1 to 99% by weight, especially 0.1 to 95% by weight of active ingredient of formula I, Ia or mixtures thereof, 99.9 to 1% by weight, especially 99.8 to 5% by weight of a solid or liquid admixture, including 0 to 25% by weight, especially 0.1 to 25% by weight of a surfactant.

Application of the compositions according to the invention to the animals to be treated may take place topically, perorally, parenterally or subcutaneously, the composition being present in the form of solutions, emulsions, suspensions, (drenches), powders, tablets, boli, capsules and pour-on formulations.

The pour-on or spot-on method consists in applying the compound of formula I to a specific location of the skin or coat, advantageously to the neck or backbone of the animal. This takes place e.g. by applying a swab or spray of the pour-on or spot-on formulation to a relatively small area of the coat, from where the active substance is dispersed almost automatically over wide areas of the fur owing to the spreading nature of the components in the formulation and assisted by the animal's movements.

Pour-on or spot-on formulations suitably contain carriers, which promote rapid dispersement over the skin surface or in the coat of the host animal, and are generally regarded as spreading oils. Suitable carriers are e.g. oily solutions; alcoholic and isopropanolic solutions such as solutions of 2-octyldodecanol or oleyl alcohol; solutions in esters of monocarboxylic acids, such as isopropyl myristate, isopropyl palmitate, lauric acid oxalate, oleic acid oleyl ester, oleic acid decyl ester, hexyl laurate, oleyl oleate, decyl oleate, capric acid esters of saturated fat alcohols of chain length C₁₂-C₁₈; solutions of esters of dicarboxylic acids, such as dibutyl phthalate, diisopropyl isophthalate, adipic acid diisopropyl ester, di-n-butyl adipate or also solutions of esters of aliphatic acids, e.g. glycols. It may be advantageous for a dispersing agent to be additionally present, such as one known from the pharmaceutical or cosmetic industry. Examples are 2-pyrrolidone, 2-(N-alkyl)pyrrolidone, acetone, polyethylene glycol and the ethers and esters thereof, propylene glycol or synthetic triglycerides.

The oily solutions include e.g. vegetable oils such as olive oil, groundnut oil, sesame oil, pine oil, linseed oil or castor oil. The vegetable oils may also be present in epoxidised form. Paraffins and silicone oils may also be used.

A pour-on or spot-on formulation generally contains 1 to 20% by weight of a compound of formula I, 0.1 to 50% by weight of dispersing agent and 45 to 98.9% by weight of solvent.

The pour-on or spot-on method is especially advantageous for use on herd animals such as cattle, horses, sheep or pigs, in which it is difficult or time-consuming to treat all the animals orally or by injection. Because of its simplicity, this method can of course also be used for all other animals, including individual domestic animals or pets, and is greatly favoured by the keepers of the animals, as it can often be carried out without the specialist presence of the veterinarian.

Whereas it is preferred to formulate commercial products as concentrates, the end user will normally use dilute formulations.

Such compositions may also contain further additives, such as stabilisers, anti-foaming agents, viscosity regulators, binding agents or tackifiers, as well as other active ingredients, in order to achieve special effects.

Anthelminthic compositions of this type, which are used by the end user, similarly form a constituent of the present invention.

In each of the processes according to the invention for pest control or in each of the pest control compositions according to the invention, the active ingredients of formula I can be used in all of their steric configurations or in mixtures thereof.

The invention also includes a method of prophylactically protecting warm-blooded animals, especially productive livestock, domestic animals and pets, against parasitic helminths, which is characterised in that the active ingredients of formula I or the active ingredient formulations prepared therefrom are administered to the animals as an additive to the feed, or to the drinks or also in solid or liquid form, orally or by injection or parenterally. The invention also includes the compounds of formula I according to the invention for usage in one of the said processes.

The following examples serve merely to illustrate the invention without restricting it, the term active ingredient representing a substance listed in table 1.

In particular, preferred formulations are made up as follows:

(%=percent by weight)

Formulation Examples

1. Granulate a) b) active ingredient  5% 10% kaolin 94% — highly dispersed silicic acid  1% — attapulgite — 90%

The active ingredient is dissolved in methylene chloride, sprayed onto the carrier and the solvent subsequently concentrated by evaporation under vacuum. Granulates of this kind can be mixed with the animal feed.

2. Granulate

active ingredient  3% polyethylene glycol (mw 200)  3% kaolin 94% (mw = molecular weight)

The finely ground active ingredient is evenly applied in a mixer to the kaolin which has been moistened with polyethylene glycol. In this way, dust-free coated granules are obtained.

3. Tablets or Boli

I active ingredient 33.00% methylcellulose  0.80% silicic acid. highly dispersed  0.80% corn starch  8.40% II lactose, cryst. 22.50% corn starch 17.00% microcryst. cellulose 16.50% magnesium stearate  1.00%

-   I Methyl cellulose is stirred into water. After the material has     swollen, silicic acid is stirred in and the mixture homogeneously     suspended. The active ingredient and the corn starch are mixed. The     aqueous suspension is worked into this mixture and kneaded to a     dough. The resulting mass is granulated through a 12 M sieve and     dried. -   II All 4 excipients are mixed thoroughly. -   III The preliminary mixes obtained according to I and II are mixed     and pressed into tablets or boli.     4. Injectables

A. Oily Vehicle (Slow Release)

1. active ingredient 0.1-1.0 g groundnut oil ad 100 ml 2. active ingredient 0.1-1.0 g sesame oil ad 100 ml Preparation: The active ingredient is dissolved in part of the oil whilst stirring and, if required, with gentle heating, then after cooling made up to the desired volume and sterile-filtered through a suitable membrane filter with a pore size of 0.22 mm.

B Water-Miscible Solvent (Average Rate of Release)

active ingredient 0.1-1.0 g 4-hydroxymethyl-1,3-dioxolane (glycerol formal) 40 g 1,2-propanediol ad 100 ml active ingredient 0.1-1.0 g glycerol dimethyl ketal 40 g 1,2-propanediol ad 100 ml

Preparation: The active ingredient is dissolved in part of the solvent whilst stirring, made up to the desired volume and sterile-filtered through a suitable membrane filter with a pore size of 0.22 mm.

C. Aqueous Solubilisate (Rapid Release)

1. active ingredient 0.1-1.0 g polyethoxylated castor oil 10 g (40 ethylene oxide units) 1,2-propanediol 20 g benzyl alcohol 1 g Aqua ad inject. ad 100 ml

2. active ingredient 0.1-1.0 g polyethoxylated sorbitan 8 g monooleate (20 ethylene oxide units) 4-hydroxymethyl-1,3-dioxolane 20 g (glycerol formal) benzyl alcohol 1 g Aqua ad inject. ad 100 ml

Preparation: The active ingredient is dissolved in the solvents and the surfactant, and made up with water to the desired volume. Sterile filtration through an appropriate membrane filter of 0.22 mm pore size.

5. Pour On

A. active ingredient 5 g isopropyl myristate 10 g isopropanol ad 100 ml B active ingredient 2 g hexyl laurate 5 g medium-chained triglyceride 15 g ethanol ad 100 ml C. active ingredient 2 g oleyl oleate 5 g N-methyl-pyrrolidone 40 g isopropanol ad 100 ml

The aqueous systems may also preferably be used for oral and/or intraruminal application.

The compositions may also contain further additives, such as stabilisers, e.g. where appropriate epoxidised vegetable oils (epoxidised coconut oil, rapeseed oil, or soybean oil); antifoams, e.g. silicone oil, preservatives, viscosity regulators, binders, tackifiers, as well as fertilisers or other active ingredients to achieve special effects.

Further biologically active substances or additives, which are neutral towards the compounds of formula I and do not have a harmful effect on the host animal to be treated, as well as mineral salts or vitamins, may also be added to the described compositions.

The following examples serve to illustrate the invention. They do not limit the invention. The letter ‘h’ stands for hour.

PREPARATION EXAMPLES Example 1 4-Benzoyl-N-[1-cyano-1-methyl-2-(2-trifluoromethylphenoxy)-ethyl]-benzamide

330 mg of benzophenone-4-carboxylic acid are dissolved in 6 ml of dichloromethane, then 283 mg of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride, 18 mg of 4-dimethylaminopyridine and 222 mg of ethyldiisopropylamine are added, and stirred for 20 minutes at room temperature. 300 mg of 2-amino-2-methyl-3-(2-trifluoromethylphenoxy)-propionitrile are subsequently added, and the mixture stirred for a further 40 hours. Afterwards, the mixed solution is washed with an aqueous sodium bicarbonate solution, then with a 1 n hydrochloric acid solution and finally with a saturated sodium chloride solution. The organic phase is then separated, dried with sodium sulphate, filtered and concentrated by evaporation. After recrystallisation in diethylether, the residue yields 372 mg of the title compound with a melting point of 121-123° C.

The substances named in the following table may also be prepared analogously to the above-described method. The values of the melting points are indicated in ° C. Bd signifies a direct bond, so that “Bd 3-Ar₁” signifies a bond between the 3-position on the phenyl ring and Ar₁.

TABLE 1

No. Ar₁ Ar₂ W Q₁ n Q₂ phys. data 1.1 C₆H₅ C₆H₅ O 4-CH₂ 0 1.2 C₆H₅ C₆H₅ O 3-CH₂ 0 1.3 C₆H₅ C₆H₅ O 2-CH₂ 0 1.4 C₆H₅ C₆H₅ O 4-OCH₂ 0 1.5 C₆H₅ C₆H₅ O 3-OCH₂ 0 1.6 C₆H₅ C₆H₅ O 2-OCH₂ 0 1.7 C₆H₅ C₆H₅ O 4-S 0 1.8 C₆H₅ C₆H₅ O 3-S 0 1.9 C₆H₅ C₆H₅ O 2-S 0 1.10 C₆H₅ C₆H₅ O 4-S(O) 0 1.11 C₆H₅ C₆H₅ O 3-S(O) 0 1.12 C₆H₅ C₆H₅ O 2-S(O) 0 1.13 C₆H₅ C₆H₅ O 4-C(O) 0 1.14 C₆H₄ C₆H₅ O 4-C(O) 1 Bd 3-Ar₁ 1.15 C₆H₄ C₆H₅ O 4-C(O) 1 3-C(O) 1.16 C₆H₄ C₆H₅ O 4-C(O) 1 3-S(O₂) 1.17 C₆H₅ C₆H₅ O 3-C(O) 0 1.18 C₆H₄ C₆H₅ O 3-C(O) 1 Bd 4-Ar₁ 1.19 C₆H₄ C₆H₅ O 3-C(O) 1 4-S(O₂) 1.20 C₆H₅ C₆H₅ O 2-C(O) 0 1.21 C₆H₄ C₆H₅ O 2-C(O) 1 Bd 3-Ar₁ 1.22 C₆H₄ C₆H₅ O 2-C(O) 1 3-C(O) 1.23 C₆H₄ C₆H₅ O 2-C(O) 1 3-S(O₂) 1.24 C₆H₅ C₆H₅ S 4-CH₂ 0 1.25 C₆H₅ C₆H₅ S 3-CH₂ 0 1.26 C₆H₅ C₆H₅ S 2-CH₂ 0 1.27 C₆H₅ C₆H₅ S 4-OCH₂ 0 1.28 C₆H₅ C₆H₅ S 3-OCH₂ 0 1.29 C₆H₅ C₆H₅ S 2-OCH₂ 0 1.30 C₆H₅ C₆H₅ S 4-S 0 1.31 C₆H₅ C₆H₅ S 3-S 0 1.32 C₆H₅ C₆H₅ S 2-S 0 1.33 C₆H₅ C₆H₅ S 4-S(O) 0 1.34 C₆H₅ C₆H₅ S 3-S(O) 0 1.35 C₆H₅ C₆H₅ S 2-S(O) 0 1.36 C₆H₅ C₆H₅ S 4-C(O) 0 1.37 C₆H₄ C₆H₅ S 4-C(O) 1 Bd 3-Ar₁ 1.38 C₆H₄ C₆H₅ S 4-C(O) 1 3-C(O) 1.39 C₆H₄ C₆H₅ S 4-C(O) 1 3-S(O₂) 1.40 C₆H₅ C₆H₅ S 3-C(O) 0 1.41 C₆H₄ C₆H₅ S 3-C(O) 1 Bd 4-Ar₁ 1.42 C₆H₄ C₆H₅ S 3-C(O) 1 4-S(O₂) 1.43 C₆H₅ C₆H₅ S 2-C(O) 0 1.44 C₆H₄ C₆H₅ S 2-C(O) 1 Bd 3-Ar₁ 1.45 C₆H₄ C₆H₅ S 2-C(O) 1 3-C(O) 1.46 C₆H₄ C₆H₅ S 2-C(O) 1 3-S(O₂) 1.47 C₆H₅ C₆H₄-2-Cl O 4-CH₂ 0 1.48 C₆H₅ C₆H₄-2-Cl O 3-CH₂ 0 1.49 C₆H₅ C₆H₄-2-Cl O 2-CH₂ 0 1.50 C₆H₅ C₆H₄-2-Cl O 4-OCH₂ 0 1.51 C₆H₅ C₆H₄-2-Cl O 3-OCH₂ 0 1.52 C₆H₅ C₆H₄-2-Cl O 2-OCH₂ 0 1.53 C₆H₅ C₆H₄-2-Cl O 4-S 0 1.54 C₆H₅ C₆H₄-2-Cl O 3-S 0 1.55 C₆H₅ C₆H₄-2-Cl O 2-S 0 1.56 C₆H₅ C₆H₄-2-Cl O 4-S(O) 0 1.57 C₆H₅ C₆H₄-2-Cl O 3-S(O) 0 1.58 C₆H₅ C₆H₄-2-Cl O 2-S(O) 0 1.59 C₆H₅ C₆H₄-2-Cl O 4-C(O) 0 m.p. 90-3° 1.60 C₆H₄ C₆H₄-2-Cl O 4-C(O) 1 Bd 3-Ar₁ 1.61 C₆H₄ C₆H₄-2-Cl O 4-C(O) 1 3-C(O) 1.62 C₆H₄ C₆H₄-2-Cl O 4-C(O) 1 3-S(O₂) 1.63 C₆H₅ C₆H₄-2-Cl O 3-C(O) 0 1.64 C₆H₄ C₆H₄-2-Cl O 3-C(O) 1 Bd 4-Ar₁ 1.65 C₆H₄ C₆H₄-2-Cl O 3-C(O) 1 4-S(O₂) 1.66 C₆H₅ C₆H₄-2-Cl O 2-C(O) 0 1.67 C₆H₄ C₆H₄-2-Cl O 2-C(O) 1 Bd 3-Ar₁ 1.68 C₆H₄ C₆H₄-2-Cl O 2-C(O) 1 3-C(O) 1.69 C₆H₄ C₆H₄-2-Cl O 2-C(O) 1 3-S(O₂) 1.70 C₆H₅ C₆H₄-2-Cl S 4-CH₂ 0 1.71 C₆H₅ C₆H₄-2-Cl S 3-CH₂ 0 1.72 C₆H₅ C₆H₄-2-Cl S 2-CH₂ 0 1.73 C₆H₅ C₆H₄-2-Cl S 4-OCH₂ 0 1.74 C₆H₅ C₆H₄-2-Cl S 3-OCH₂ 0 1.75 C₆H₅ C₆H₄-2-Cl S 2-OCH₂ 0 1.76 C₆H₅ C₆H₄-2-Cl S 4-S 0 1.77 C₆H₅ C₆H₄-2-Cl S 3-S 0 1.78 C₆H₅ C₆H₄-2-Cl S 2-S 0 1.79 C₆H₅ C₆H₄-2-Cl S 4-S(O) 0 1.80 C₆H₅ C₆H₄-2-Cl S 3-S(O) 0 1.81 C₆H₅ C₆H₄-2-Cl S 2-S(O) 0 1.82 C₆H₅ C₆H₄-2-Cl S 4-C(O) 0 m.p. 109-10° 1.83 C₆H₄ C₆H₄-2-Cl S 4-C(O) 1 Bd 3-Ar₁ 1.84 C₆H₄ C₆H₄-2-Cl S 4-C(O) 1 3-C(O) 1.85 C₆H₄ C₆H₄-2-Cl S 4-C(O) 1 3-S(O₂) 1.86 C₆H₅ C₆H₄-2-Cl S 3-C(O) 0 1.87 C₆H₄ C₆H₄-2-Cl S 3-C(O) 1 Bd 4-Ar₁ 1.88 C₆H₄ C₆H₄-2-Cl S 3-C(O) 1 4-S(O₂) 1.89 C₆H₅ C₆H₄-2-Cl S 2-C(O) 0 1.90 C₆H₄ C₆H₄-2-Cl S 2-C(O) 1 Bd 3-Ar₁ 1.91 C₆H₄ C₆H₄-2-Cl S 2-C(O) 1 3-C(O) 1.92 C₆H₄ C₆H₄-2-Cl S 2-C(O) 1 3-S(O₂) 1.93 C₆H₅ C₆H₄-2-CF₃ O 4-CH₂ 0 1.94 C₆H₅ C₆H₄-2-CF₃ O 3-CH₂ 0 1.95 C₆H₅ C₆H₄-2-CF₃ O 2-CH₂ 0 1.96 C₆H₅ C₆H₄-2-CF₃ O 4-OCH₂ 0 m.p. 44-8° 1.97 C₆H₅ C₆H₄-2-CF₃ O 3-OCH₂ 0 1.98 C₆H₅ C₆H₄-2-CF₃ O 2-OCH₂ 0 1.99 C₆H₅ C₆H₄-2-CF₃ O 4-S 0 1.100 C₆H₅ C₆H₄-2-CF₃ O 3-S 0 1.101 C₆H₅ C₆H₄-2-CF₃ O 2-S 0 1.102 C₆H₅ C₆H₄-2-CF₃ O 4-S(O) 0 1.103 C₆H₅ C₆H₄-2-CF₃ O 3-S(O) 0 1.104 C₆H₅ C₆H₄-2-CF₃ O 2-S(O) 0 1.105 C₆H₅ C₆H₄-2-CF₃ O 4-C(O) 0 m.p. 121-3° 1.106 C₆H₄ C₆H₄-2-CF₃ O 4-C(O) 1 Bd 3-Ar₁ 1.107 C₆H₄ C₆H₄-2-CF₃ O 4-C(O) 1 3-C(O) m.p. 74-8° 1.108 C₆H₄ C₆H₄-2-CF₃ O 4-C(O) 1 3-S(O₂) m.p. 207-10° 1.109 C₆H₅ C₆H₄-2-CF₃ O 3-C(O) 0 1.110 C₆H₄ C₆H₄-2-CF₃ O 3-C(O) 1 Bd 4-Ar₁ m.p. 90-3° 1.111 C₆H₄ C₆H₄-2-CF₃ O 3-C(O) 1 4-S(O₂) 1.112 C₆H₅ C₆H₄-2-CF₃ O 2-C(O) 0 1.113 C₆H₄ C₆H₄-2-CF₃ O 2-C(O) 1 Bd 3-Ar₁ 1.114 C₆H₄ C₆H₄-2-CF₃ O 2-C(O) 1 3-C(O) 1.115 C₆H₄ C₆H₄-2-CF₃ O 2-C(O) 1 3-S(O₂) 1.116 C₆H₅ C₆H₄-2-CF₃ S 4-CH₂ 0 1.117 C₆H₅ C₆H₄-2-CF₃ S 3-CH₂ 0 1.118 C₆H₅ C₆H₄-2-CF₃ S 2-CH₂ 0 1.119 C₆H₅ C₆H₄-2-CF₃ S 4-OCH₂ 0 1.120 C₆H₅ C₆H₄-2-CF₃ S 3-OCH₂ 0 1.121 C₆H₅ C₆H₄-2-CF₃ S 2-OCH₂ 0 1.122 C₆H₅ C₆H₄-2-CF₃ S 4-S 0 1.123 C₆H₅ C₆H₄-2-CF₃ S 3-S 0 1.124 C₆H₅ C₆H₄-2-CF₃ S 2-S 0 1.125 C₆H₅ C₆H₄-2-CF₃ S 4-S(O) 0 1.126 C₆H₅ C₆H₄-2-CF₃ S 3-S(O) 0 1.127 C₆H₅ C₆H₄-2-CF₃ S 2-S(O) 0 1.128 C₆H₅ C₆H₄-2-CF₃ S 4-C(O) 0 1.129 C₆H₄ C₆H₄-2-CF₃ S 4-C(O) 1 Bd 3-Ar₁ 1.130 C₆H₄ C₆H₄-2-CF₃ S 4-C(O) 1 3-C(O) 1.131 C₆H₄ C₆H₄-2-CF₃ S 4-C(O) 1 3-S(O₂) 1.132 C₆H₅ C₆H₄-2-CF₃ S 3-C(O) 0 1.133 C₆H₄ C₆H₄-2-CF₃ S 3-C(O) 1 Bd 4-Ar₁ 1.134 C₆H₄ C₆H₄-2-CF₃ S 3-C(O) 1 4-S(O₂) 1.135 C₆H₅ C₆H₄-2-CF₃ S 2-C(O) 0 1.136 C₆H₄ C₆H₄-2-CF₃ S 2-C(O) 1 Bd 3-Ar₁ 1.137 C₆H₄ C₆H₄-2-CF₃ S 2-C(O) 1 3-C(O) 1.138 C₆H₄ C₆H₄-2-CF₃ S 2-C(O) 1 3-S(O₂) 1.139 C₆H₄-4-F C₆H₅ O 4-CH₂ 0 1.140 C₆H₄-4-F C₆H₅ O 3-CH₂ 0 1.141 C₆H₄-4-F C₆H₅ O 2-CH₂ 0 1.142 C₆H₄-4-F C₆H₅ O 4-OCH₂ 0 1.143 C₅H₄-4-F C₆H₅ O 3-OCH₂ 0 1.144 C₆H₄-4-F C₆H₅ O 2-OCH₂ 0 1.145 C₆H₄-4-F C₆H₅ O 4-S 0 1.146 C₆H₄-4-F C₆H₅ O 3-S 0 1.147 C₆H₄-4-F C₆H₅ O 2-S 0 1.148 C₆H₄-4-F C₆H₅ O 4-S(O) 0 1.149 C₆H₄-4-F C₆H₅ O 3-S(O) 0 1.150 C₆H₄-4-F C₆H₅ O 2-S(O) 0 1.151 C₆H₄-4-F C₆H₅ O 4-C(O) 0 1.152 C₆H₃-4-F C₆H₅ O 4-C(O) 1 Bd 3-Ar₁ 1.153 C₆H₃-4-F C₆H₅ O 4-C(O) 1 3-C(O) 1.154 C₆H₃-4-F C₆H₅ O 4-C(O) 1 3-S(O₂) 1.155 C₆H₄-4-F C₆H₅ O 3-C(O) 0 1.156 C₆H₃-4-F C₆H₅ O 3-C(O) 1 Bd 4-Ar₁ 1.157 C₆H₃-4-F C₆H₅ O 3-C(O) 1 4-S(O₂) 1.158 C₆H₄-4-F C₆H₅ O 2-C(O) 0 1.159 C₆H₃-4-F C₆H₅ O 2-C(O) 1 Bd 3-Ar₁ 1.160 C₆H₃-4-F C₆H₅ O 2-C(O) 1 3-C(O) 1.161 C₆H₃-4-F C₆H₅ O 2-C(O) 1 3-S(O₂) 1.162 C₆H₄-4-F C₆H₅ S 4-CH₂ 0 1.163 C₆H₄-4-F C₆H₅ S 3-CH₂ 0 1.164 C₆H₄-4-F C₆H₅ S 2-CH₂ 0 1.165 C₆H₄-4-F C₆H₅ S 4-OCH₂ 0 1.166 C₆H₄-4-F C₆H₅ S 3-OCH₂ 0 1.167 C₆H₄-4-F C₆H₅ S 2-OCH₂ 0 1.168 C₆H₄-4-F C₆H₅ S 4-S 0 1.169 C₆H₄-4-F C₆H₅ S 3-S 0 1.170 C₆H₄-4-F C₆H₅ S 2-S 0 1.171 C₆H₄-4-F C₆H₅ S 4-S(O) 0 1.172 C₆H₄-4-F C₆H₅ S 3-S(O) 0 1.173 C₆H₄-4-F C₆H₅ S 2-S(O) 0 1.174 C₆H₄-4-F C₆H₅ S 4-C(O) 0 1.175 C₆H₃-4-F C₆H₅ S 4-C(O) 1 Bd 3-Ar₁ 1.176 C₆H₃-4-F C₆H₅ S 4-C(O) 1 3-C(O) 1.177 C₆H₃-4-F C₆H₅ S 4-C(O) 1 3-S(O₂) 1.178 C₆H₄-4-F C₆H₅ S 3-C(O) 0 1.179 C₆H₃-4-F C₆H₅ S 3-C(O) 1 Bd 4-Ar₁ 1.180 C₆H₃-4-F C₆H₅ S 3-C(O) 1 4-S(O₂) 1.181 C₆H₄-4-F C₆H₅ S 2-C(O) 0 1.182 C₆H₃-4-F C₆H₅ S 2-C(O) 1 Bd 3-Ar₁ 1.183 C₆H₃-4-F C₆H₅ S 2-C(O) 1 3-C(O) 1.184 C₆H₃-4-F C₆H₅ S 2-C(O) 1 3-S(O₂) 1.185 C₆H₄-4-F C₆H₄-2-Cl O 4-CH₂ 0 1.186 C₆H₄-4-F C₆H₄-2-Cl O 3-CH₂ 0 1.187 C₆H₄-4-F C₆H₄-2-Cl O 2-CH₂ 0 1.188 C₆H₄-4-F C₆H₄-2-Cl O 4-OCH₂ 0 1.189 C₆H₄-4-F C₆H₄-2-Cl O 3-OCH₂ 0 1.190 C₆H₄-4-F C₆H₄-2-Cl O 2-OCH₂ 0 1.191 C₆H₄-4-F C₆H₄-2-Cl O 4-S 0 1.192 C₆H₄-4-F C₆H₄-2-Cl O 3-S 0 1.193 C₆H₄-4-F C₆H₄-2-Cl O 2-S 0 1.194 C₅H₄-4-F C₆H₄-2-Cl O 4-S(O) 0 1.195 C₆H₄-4-F C₆H₄-2-Cl O 3-(O) 0 1.196 C₆H₄-4-F C₆H₄-2-Cl O 2-S(O) 0 1.197 C₆H₄-4-F C₆H₄-2-Cl O 4-C(O) 0 1.198 C₆H₃-4-F C₆H₄-2-Cl O 4-C(O) 1 Bd 3-Ar₁ 1.199 C₆H₃-4-F C₆H₄-2-Cl O 4-C(O) 1 3-C(O) 1.200 C₆H₃-4-F C₆H₄-2-Cl O 4-C(O) 1 3-S(O₂) 1.201 C₆H₄-4-F C₆H₄-2-Cl O 3-C(O) 0 1.202 C₆H₃-4-F C₆H₄-2-Cl O 3-C(O) 1 Bd 4-Ar₁ 1.203 C₆H₃-4-F C₆H₄-2-Cl O 3-C(O) 1 4-S(O₂) 1.204 C₆H₄-4-F C₆H₄-2-Cl O 2-C(O) 0 1.205 C₆H₃-4-F C₆H₄-2-Cl O 2-C(O) 1 Bd 3-Ar₁ 1.206 C₆H₃-4-F C₆H₄-2-Cl O 2-C(O) 1 3-C(O) 1.207 C₆H₃-4-F C₆H₄-2-Cl O 2-C(O) 1 3-S(O₂) 1.208 C₆H₄-4-F C₆H₄-2-Cl S 4-CH₂ 0 1.209 C₆H₄-4-F C₆H₄-2-Cl S 3-CH₂ 0 1.210 C₆H₄-4-F C₆H₄-2-Cl S 2-CH₂ 0 1.211 C₆H₄-4-F C₆H₄-2-Cl S 4-OCH₂ 0 1.212 C₆H₄-4-F C₆H₄-2-Cl S 3-OCH₂ 0 1.213 C₆H₄-4-F C₆H₄-2-Cl S 2-OCH₂ 0 1.214 C₆H₄-4-F C₆H₄-2-Cl S 4-S 0 1.215 C₆H₄-4-F C₆H₄-2-Cl S 3-S 0 1.216 C₆H₄-4-F C₆H₄-2-Cl S 2-S 0 1.217 C₆H₄-4-F C₆H₄-2-Cl S 4-S(O) 0 1.218 C₆H₄-4-F C₆H₄-2-Cl S 3-S(O) 0 1.219 C₆H₄-4-F C₆H₄-2-Cl S 2-S(O) 0 1.220 C₆H₄-4-F C₆H₄-2-Cl S 4-C(O) 0 1.221 C₆H₃-4-F C₆H₄-2-Cl S 4-C(O) 1 Bd 3-Ar₁ 1.222 C₆H₃-4-F C₆H₄-2-Cl S 4-C(O) 1 3-C(O) 1.223 C₆H₃-4-F C₆H₄-2-Cl S 4-C(O) 1 3-S(O₂) 1.224 C₆H₄-4-F C₆H₄-2-Cl S 3-C(O) 0 1.225 C₆H₃-4-F C₆H₄-2-Cl S 3-C(O) 1 Bd 4-Ar₁ 1.226 C₆H₃-4-F C₆H₄-2-Cl S 3-C(O) 1 4-S(O₂) 1.227 C₆H₄-4-F C₆H₄-2-Cl S 2-C(O) 0 1.228 C₆H₃-4-F C₆H₄-2-Cl S 2-C(O) 1 Bd 3-Ar₁ 1.229 C₆H₃-4-F C₆H₄-2-Cl S 2-C(O) 1 3-C(O) 1.230 C₆H₃-4-F C₆H₄-2-Cl S 2-C(O) 1 3-S(O₂) 1.231 C₆H₄-4-F C₆H₄-2-CF₃ O 4-CH₂ 0 1.232 C₆H₄-4-F C₆H₄-2-CF₃ O 3-CH₂ 0 1.233 C₆H₄-4-F C₆H₄-2-CF₃ O 2-CH₂ 0 1.234 C₆H₄-4-F C₆H₄-2-CF₃ O 4-OCH₂ 0 1.235 C₆H₄-4-F C₆H₄-2-CF₃ O 3-OCH₂ 0 1.236 C₆H₄-4-F C₆H₄-2-CF₃ O 2-OCH₂ 0 1.237 C₆H₄-4-F C₆H₄-2-CF₃ O 4-S 0 1.238 C₆H₄-4-F C₆H₄-2-CF₃ O 3-S 0 1.239 C₆H₄-4-F C₆H₄-2-CF₃ O 2-S 0 1.240 C₆H₄-4-F C₆H₄-2-CF₃ O 4-S(O) 0 1.241 C₆H₄-4-F C₆H₄-2-CF₃ O 3-S(O) 0 1.242 C₆H₄-4-F C₆H₄-2-CF₃ O 2-S(O) 0 1.243 C₆H₄-4-F C₆H₄-2-CF₃ O 4-C(O) 0 1.244 C₆H₃-4-F C₆H₄-2-CF₃ O 4-C(O) 1 Bd 3-Ar₁ 1.245 C₆H₃-4-F C₆H₄-2-CF₃ O 4-C(O) 1 3-C(O) 1.246 C₆H₃-4-F C₆H₄-2-CF₃ O 4-C(O) 1 3-S(O₂) 1.247 C₆H₄-4-F C₆H₄-2-CF₃ O 3-C(O) 0 1.248 C₆H₃-4-F C₆H₄-2-CF₃ O 3-C(O) 1 Bd 4-Ar₁ 1.249 C₆H₃-4-F C₆H₄-2-CF₃ O 3-C(O) 1 4-S(O₂) 1.250 C₆H₄-4-F C₆H₄-2-CF₃ O 2-C(O) 0 1.251 C₆H₃-4-F C₆H₄-2-CF₃ O 2-C(O) 1 Bd 3-Ar₁ 1.252 C₆H₃-4-F C₆H₄-2-CF₃ O 2-C(O) 1 3-C(O) 1.253 C₆H₃-4-F C₆H₄-2-CF₃ O 2-C(O) 1 3-S(O₂) 1.254 C₆H₄-4-F C₆H₄-2-CF₃ S 4-CH₂ 0 1.255 C₆H₄-4-F C₆H₄-2-CF₃ S 3-CH₂ 0 1.256 C₆H₄-4-F C₆H₄-2-CF₃ S 2-CH₂ 0 1.257 C₆H₄-4-F C₆H₄-2-CF₃ S 4-OCH₂ 0 1.258 C₆H₄-4-F C₆H₄-2-CF₃ S 3-OCH₂ 0 1.259 C₆H₄-4-F C₆H₄-2-CF₃ S 2-OCH₂ 0 1.260 C₆H₄-4-F C₆H₄-2-CF₃ S 4-S 0 1.261 C₆H₄-4-F C₆H₄-2-CF₃ S 3-S 0 1.262 C₆H₄-4-F C₆H₄-2-CF₃ S 2-S 0 1.263 C₆H₄-4-F C₆H₄-2-CF₃ S 4-S(O) 0 1.264 C₆H₄-4-F C₆H₄-2-CF₃ S 3-S(O) 0 1.265 C₆H₄-4-F C₆H₄-2-CF₃ S 2-S(O) 0 1.266 C₆H₄-4-F C₆H₄-2-CF₃ S 4-C(O) 0 1.267 C₆H₃-4-F C₆H₄-2-CF₃ S 4-C(O) 1 Bd 3-Ar₁ 1.268 C₆H₃-4-F C₆H₄-2-CF₃ S 4-C(O) 1 3-C(O) 1.269 C₆H₃-4-F C₆H₄-2-CF₃ S 4-C(O) 1 3-S(O₂) 1.270 C₆H₄-4-F C₆H₄-2-CF₃ S 3-C(O) 0 1.271 C₆H₃-4-F C₆H₄-2-CF₃ S 3-C(O) 1 Bd 4-Ar₁ 1.272 C₆H₃-4-F C₆H₄-2-CF₃ S 3-C(O) 1 4-S(O₂) 1.273 C₆H₄-4-F C₆H₄-2-CF₃ S 2-C(O) 0 1.274 C₆H₃-4-F C₆H₄-2-CF₃ S 2-C(O) 1 Bd 3-Ar₁ 1.275 C₆H₃-4-F C₆H₄-2-CF₃ S 2-C(O) 1 3-C(O) 1.276 C₆H₃-4-F C₆H₄-2-CF₃ S 2-C(O) 1 3-S(O₂) 1.277 C₆H₄-4-Cl C₆H₅ O 4-CH₂ 0 1.278 C₆H₄-4-Cl C₆H₅ O 3-CH₂ 0 1.279 C₆H₄-4-Cl C₆H₅ O 2-CH₂ 0 1.280 C₆H₄-4-Cl C₆H₅ O 4-OCH₂ 0 1.281 C₆H₄-4-Cl C₆H₅ O 3-OCH₂ 0 1.282 C₆H₄-4-Cl C₆H₅ O 2-OCH₂ 0 1.283 C₆H₄-4-Cl C₆H₅ O 4-S 0 1.284 C₆H₄-4-Cl C₆H₅ O 3-S 0 1.285 C₆H₄-4-Cl C₆H₅ O 2-S 0 1.286 C₆H₄-4-Cl C₆H₅ O 4-S(O) 0 1.287 C₆H₄-4-Cl C₆H₅ O 3-S(O) 0 1.288 C₆H₄-4-Cl C₆H₅ O 2-S(O) 0 1.289 C₆H₄-4-Cl C₆H₅ O 4-C(O) 0 1.290 C₆H₃-4-Cl C₆H₅ O 4-C(O) 1 Bd 3-Ar₁ 1.291 C₆H₃-4-Cl C₆H₅ O 4-C(O) 1 3-C(O) 1.292 C₆H₃-4-Cl C₆H₅ O 4-C(O) 1 3-S(O₂) 1.293 C₆H₄-4-Cl C₆H₅ O 3-C(O) 0 1.294 C₆H₃-4-Cl C₆H₅ O 3-C(O) 1 Bd 4-Ar₁ 1.295 C₆H₃-4-Cl C₆H₅ O 3-C(O) 1 4-S(O₂) 1.296 C₆H₄-4-Cl C₆H₅ O 2-C(O) 0 1.297 C₆H₃-4-Cl C₆H₅ O 2-C(O) 1 Bd 3-Ar₁ 1.298 C₆H₃-4-Cl C₆H₅ O 2-C(O) 1 3-C(O) 1.299 C₆H₃-4-Cl C₆H₅ O 2-C(O) 1 3-S(O₂) 1.300 C₆H₄-4-Cl C₆H₅ S 4-CH₂ 0 1.301 C₆H₄-4-Cl C₆H₅ S 3-CH₂ 0 1.302 C₆H₄-4-Cl C₆H₅ S 2-CH₂ 0 1.303 C₆H₄-4-Cl C₆H₅ S 4-OCH₂ 0 1.304 C₆H₄-4-Cl C₆H₅ S 3-OCH₂ 0 1.305 C₆H₄-4-Cl C₆H₅ S 2-OCH₂ 0 1.306 C₆H₄-4-Cl C₆H₅ S 4-S 0 1.307 C₆H₄-4-Cl C₆H₅ S 3-S 0 1.308 C₆H₄-4-Cl C₆H₅ S 2-S 0 1.309 C₆H₄-4-Cl C₆H₅ S 4-S(O) 0 1.310 C₆H₄-4-Cl C₆H₅ S 3-S(O) 0 1.311 C₆H₄-4-Cl C₆H₅ S 2-S(O) 0 1.312 C₆H₄-4-Cl C₆H₅ S 4-C(O) 0 1.313 C₆H₃-4-Cl C₆H₅ S 4-C(O) 1 Bd 3-Ar₁ 1.314 C₆H₃-4-Cl C₆H₅ S 4-C(O) 1 3-C(O) 1.315 C₆H₃-4-Cl C₆H₅ S 4-C(O) 1 3-S(O₂) 1.316 C₆H₄-4-Cl C₆H₅ S 3-C(O) 0 1.317 C₆H₃-4-Cl C₆H₅ S 3-C(O) 1 Bd 4-Ar₁ 1.318 C₆H₃-4-Cl C₆H₅ S 3-C(O) 1 4-S(O₂) 1.319 C₆H₄-4-Cl C₆H₅ S 2-C(O) 0 1.320 C₆H₃-4-Cl C₆H₅ S 2-C(O) 1 Bd 3-Ar₁ 1.321 C₆H₃-4-Cl C₆H₅ S 2-C(O) 1 3-C(O) 1.322 C₆H₃-4-Cl C₆H₅ S 2-C(O) 1 3-S(O₂) 1.323 C₆H₄-4-Cl C₆H₄-2-Cl O 4-CH₂ 0 1.324 C₆H₄-4-Cl C₆H₄-2-Cl O 3-CH₂ 0 1.325 C₆H₄-4-Cl C₆H₄-2-Cl O 2-CH₂ 0 1.326 C₆H₄-4-Cl C₆H₄-2-Cl O 4-OCH₂ 0 1.327 C₆H₄-4-Cl C₆H₄-2-Cl O 3-OCH₂ 0 1.328 C₆H₄-4-Cl C₆H₄-2-Cl O 2-OCH₂ 0 1.329 C₆H₄-4-Cl C₆H₄-2-Cl O 4-S 0 1.330 C₆H₄-4-Cl C₆H₄-2-Cl O 3-S 0 1.331 C₆H₄-4-Cl C₆H₄-2-Cl O 2-S 0 1.332 C₆H₄-4-Cl C₆H₄-2-Cl O 4-S(O) 0 1.333 C₆H₄-4-Cl C₆H₄-2-Cl O 3-S(O) 0 1.334 C₆H₄-4-Cl C₆H₄-2-Cl O 2-S(O) 0 1.335 C₆H₄-4-Cl C₆H₄-2-Cl O 4-C(O) 0 1.336 C₆H₃-4-Cl C₆H₄-2-Cl O 4-C(O) 1 Bd 3-Ar₁ 1.337 C₆H₃-4-Cl C₆H₄-2-Cl O 4-C(O) 1 3-C(O) 1.338 C₆H₃-4-Cl C₆H₄-2-Cl O 4-C(O) 1 3-S(O₂) 1.339 C₆H₄-4-Cl C₆H₄-2-Cl O 3-C(O) 0 1.340 C₆H₃-4-Cl C₆H₄-2-Cl O 3-C(O) 1 Bd 4-Ar₁ 1.341 C₆H₃-4-Cl C₆H₄-2-Cl O 3-C(O) 1 4-S(O₂) 1.342 C₆H₄-4-Cl C₆H₄-2-Cl O 2-C(O) 0 1.343 C₆H₃-4-Cl C₆H₄-2-Cl O 2-C(O) 1 Bd 3-Ar₁ 1.344 C₆H₃-4-Cl C₆H₄-2-Cl O 2-C(O) 1 3-C(O) 1.345 C₆H₃-4-Cl C₆H₄-2-Cl O 2-C(O) 1 3-S(O₂) 1.346 C₆H₄-4-Cl C₆H₄-2-Cl S 4-CH₂ 0 1.347 C₆H₄-4-Cl C₆H₄-2-Cl S 3-CH₂ 0 1.348 C₆H₄-4-Cl C₆H₄-2-Cl S 2-CH₂ 0 1.349 C₆H₄-4-Cl C₆H₄-2-Cl S 4-OCH₂ 0 1.350 C₆H₄-4-Cl C₆H₄-2-Cl S 3-OCH₂ 0 1.351 C₆H₄-4-Cl C₆H₄-2-Cl S 2-OCH₂ 0 1.352 C₆H₄-4-Cl C₆H₄-2-Cl S 4-S 0 1.353 C₆H₄-4-Cl C₆H₄-2-Cl S 3-S 0 1.354 C₆H₄-4-Cl C₆H₄-2-Cl S 2-S 0 1.355 C₆H₄-4-Cl C₆H₄-2-Cl S 4-S(O) 0 1.356 C₆H₄-4-Cl C₆H₄-2-Cl S 3-S(O) 0 1.357 C₆H₄-4-Cl C₆H₄-2-Cl S 2-S(O) 0 1.358 C₆H₄-4-Cl C₆H₄-2-Cl S 4-C(O) 0 1.359 C₆H₃-4-Cl C₆H₄-2-Cl S 4-C(O) 1 Bd 3-Ar₁ 1.360 C₆H₃-4-Cl C₆H₄-2-Cl S 4-C(O) 1 3-C(O) 1.361 C₆H₃-4-Cl C₆H₄-2-Cl S 4-C(O) 1 3-S(O₂) 1.362 C₆H₄-4-Cl C₆H₄-2-Cl S 3-C(O) 0 1.363 C₆H₃-4-Cl C₆H₄-2-Cl S 3-C(O) 1 Bd 4-Ar₁ 1.364 C₆H₃-4-Cl C₆H₄-2-Cl S 3-C(O) 1 4-S(O₂) 1.365 C₆H₄-4-Cl C₆H₄-2-Cl S 2-C(O) 0 1.366 C₆H₃-4-Cl C₆H₄-2-Cl S 2-C(O) 1 Bd 3-Ar₁ 1.367 C₆H₃-4-Cl C₆H₄-2-Cl S 2-C(O) 1 3-C(O) 1.368 C₆H₃-4-Cl C₆H₄-2-Cl S 2-C(O) 1 3-S(O₂) 1.369 C₆H₄-4-Cl C₆H₄-2-CF₃ O 4-CH₂ 0 1.370 C₆H₄-4-Cl C₆H₄-2-CF₃ O 3-CH₂ 0 1.371 C₆H₄-4-Cl C₆H₄-2-CF₃ O 2-CH₂ 0 1.372 C₆H₄-4-Cl C₆H₄-2-CF₃ O 4-OCH₂ 0 1.373 C₆H₄-4-Cl C₆H₄-2-CF₃ O 3-OCH₂ 0 1.374 C₆H₄-4-Cl C₆H₄-2-CF₃ O 2-OCH₂ 0 1.375 C₆H₄-4-Cl C₆H₄-2-CF₃ O 4-S 0 1.376 C₆H₄-4-Cl C₆H₄-2-CF₃ O 3-S 0 1.377 C₆H₄-4-Cl C₆H₄-2-CF₃ O 2-S 0 1.378 C₆H₄-4-Cl C₆H₄-2-CF₃ O 4-S(O) 0 1.379 C₆H₄-4-Cl C₆H₄-2-CF₃ O 3-S(O) 0 1.380 C₆H₄-4-Cl C₆H₄-2-CF₃ O 2-S(O) 0 1.381 C₆H₄-4-Cl C₆H₄-2-CF₃ O 4-C(O) 0 1.382 C₆H₃-4-Cl C₆H₄-2-CF₃ O 4-C(O) 1 Bd 3-Ar₁ 1.383 C₆H₃-4-Cl C₆H₄-2-CF₃ O 4-C(O) 1 3-C(O) 1.384 C₆H₃-4-Cl C₆H₄-2-CF₃ O 4-C(O) 1 3-S(O₂) 1.385 C₆H₄-4-Cl C₆H₄-2-CF₃ O 3-C(O) 0 1.386 C₆H₃-4-Cl C₆H₄-2-CF₃ O 3-C(O) 1 Bd 4-Ar₁ 1.387 C₆H₃-4-Cl C₆H₄-2-CF₃ O 3-C(O) 1 4-S(O₂) 1.388 C₆H₄-4-Cl C₆H₄-2-CF₃ O 2-C(O) 0 1.389 C₆H₃-4-Cl C₆H₄-2-CF₃ O 2-C(O) 1 Bd 3-Ar₁ 1.390 C₆H₃-4-Cl C₆H₄-2-CF₃ O 2-C(O) 1 3-C(O) 1.391 C₆H₃-4-Cl C₆H₄-2-CF₃ O 2-C(O) 1 3-S(O₂) 1.392 C₆H₄-4-Cl C₆H₄-2-CF₃ S 4-CH₂ 0 1.393 C₆H₄-4-Cl C₆H₄-2-CF₃ S 3-CH₂ 0 1.394 C₆H₄-4-Cl C₆H₄-2-CF₃ S 2-CH₂ 0 1.395 C₆H₄-4-Cl C₆H₄-2-CF₃ S 4-OCH₂ 0 1.396 C₆H₄-4-Cl C₆H₄-2-CF₃ S 3-OCH₂ 0 1.397 C₆H₄-4-Cl C₆H₄-2-CF₃ S 2-OCH₂ 0 1.398 C₆H₄-4-Cl C₆H₄-2-CF₃ S 4-S 0 1.399 C₆H₄-4-Cl C₆H₄-2-CF₃ S 3-S 0 1.400 C₆H₄-4-Cl C₆H₄-2-CF₃ S 2-S 0 1.401 C₆H₄-4-Cl C₆H₄-2-CF₃ S 4-S(O) 0 1.402 C₆H₄-4-Cl C₆H₄-2-CF₃ S 3-S(O) 0 1.403 C₆H₄-4-Cl C₆H₄-2-CF₃ S 2-S(O) 0 1.404 C₆H₄-4-Cl C₆H₄-2-CF₃ S 4-C(O) 0 1.405 C₆H₃-4-Cl C₆H₄-2-CF₃ S 4-C(O) 1 Bd 3-Ar₁ 1.406 C₆H₃-4-Cl C₆H₄-2-CF₃ S 4-C(O) 1 3-C(O) 1.407 C₅H₃-4-Cl C₆H₄-2-CF₃ S 4-C(O) 1 3-S(O₂) 1.408 C₆H₄-4-Cl C₆H₄-2-CF₃ S 3-C(O) 0 1.409 C₆H₃-4-Cl C₆H₄-2-CF₃ S 3-C(O) 1 Bd 4-Ar₁ 1.410 C₆H₃-4-Cl C₆H₄-2-CF₃ S 3-C(O) 1 4-S(O₂) 1.411 C₆H₄-4-Cl C₆H₄-2-CF₃ S 2-C(O) 0 1.412 C₆H₃-4-Cl C₆H₄-2-CF₃ S 2-C(O) 1 Bd 3-Ar₁ 1.413 C₆H₃-4-Cl C₆H₄-2-CF₃ S 2-C(O) 1 3-C(O) 1.414 C₆H₃-4-Cl C₆H₄-2-CF₃ S 2-C(O) 1 3-S(O₂) 1.415 C₆H₄-4-CH₃ C₆H₅ O 4-CH₂ 0 1.416 C₆H₄-4-CH₃ C₆H₅ O 3-CH₂ 0 1.417 C₆H₄-4-CH₃ C₆H₅ O 2-CH₂ 0 1.418 C₆H₄-4-CH₃ C₆H₅ O 4-OCH₂ 0 1.419 C₆H₄-4-CH₃ C₆H₅ O 3-OCH₂ 0 1.420 C₆H₄-4-CH₃ C₆H₅ O 2-OCH₂ 0 1.421 C₆H₄-4-CH₃ C₆H₅ O 4-S 0 1.422 C₆H₄-4-CH₃ C₆H₅ O 3-S 0 1.423 C₆H₄-4-CH₃ C₆H₅ O 2-S 0 1.424 C₆H₄-4-CH₃ C₆H₅ O 4-S(O) 0 1.425 C₆H₄-4-CH₃ C₆H₅ O 3-S(O) 0 1.426 C₆H₄-4-CH₃ C₆H₅ O 2-S(O) 0 1.427 C₆H₄-4-CH₃ C₆H₅ O 4-C(O) 0 1.428 C₆H₃-4-CH₃ C₆H₅ O 4-C(O) 1 Bd 3-Ar₁ 1.429 C₆H₃-4-CH₃ C₆H₅ O 4-C(O) 1 3-C(O) 1.430 C₆H₃-4-CH₃ C₆H₅ O 4-C(O) 1 3-S(O₂) 1.431 C₆H₃-4-CH₃ C₆H₅ O 3-C(O) 0 1.432 C₆H₃-4-CH₃ C₆H₅ O 3-C(O) 1 Bd 4-Ar₁ 1.433 C₆H₃-4-CH₃ C₆H₅ O 3-C(O) 1 4-S(O₂) 1.434 C₆H₄-4-CH₃ C₆H₅ O 2-C(O) 0 1.435 C₆H₃-4-CH₃ C₆H₅ O 2-C(O) 1 Bd 3-Ar₁ 1.436 C₆H₃-4-CH₃ C₆H₅ O 2-C(O) 1 3-C(O) 1.437 C₆H₃-4-CH₃ C₆H₅ O 2-C(O) 1 3-S(O₂) 1.438 C₆H₄-4-CH₃ C₆H₅ S 4-CH₂ 0 1.439 C₆H₄-4-CH₃ C₆H₅ S 3-CH₂ 0 1.440 C₆H₄-4-CH₃ C₆H₅ S 2-CH₂ 0 1.441 C₆H₄-4-CH₃ C₆H₅ S 4-OCH₂ 0 1.442 C₆H₄-4-CH₃ C₆H₅ S 3-OCH₂ 0 1.443 C₆H₄-4-CH₃ C₆H₅ S 2-OCH₂ 0 1.444 C₆H₄-4-CH₃ C₆H₅ S 4-S 0 1.445 C₆H₄-4-CH₃ C₆H₅ S 3-S 0 1.446 C₆H₄-4-CH₃ C₆H₅ S 2-S 0 1.447 C₆H₄-4-CH₃ C₆H₅ S 4-S(O) 0 1.448 C₆H₄-4-CH₃ C₆H₅ S 3-S(O) 0 1.449 C₆H₄-4-CH₃ C₆H₅ S 2-S(O) 0 1.450 C₆H₄-4-CH₃ C₆H₅ S 4-C(O) 0 1.451 C₆H₃-4-CH₃ C₆H₅ S 4-C(O) 1 Bd 3-Ar₁ 1.452 C₆H₃-4-CH₃ C₆H₅ S 4-C(O) 1 3-C(O) 1.453 C₆H₃-4-CH₃ C₆H₅ S 4-C(O) 1 3-S(O₂) 1.454 C₆H₃-4-CH₃ C₆H₅ S 3-C(O) 0 1.455 C₆H₃-4-CH₃ C₆H₅ S 3-C(O) 1 Bd 4-Ar₁ 1.456 C₆H₃-4-CH₃ C₆H₅ S 3-C(O) 1 4-S(O₂) 1.457 C₆H₄-4-CH₃ C₆H₅ S 2-C(O) 0 1.458 C₆H₃-4-CH₃ C₆H₅ S 2-C(O) 1 Bd 3-Ar₁ 1.459 C₆H₃-4-CH₃ C₆H₅ S 2-C(O) 1 3-C(O) 1.460 C₆H₃-4-CH₃ C₆H₅ S 2-C(O) 1 3-S(O₂) 1.461 C₆H₄-4-CH₃ C₆H₄-2-Cl O 4-CH₂ 0 1.462 C₆H₄-4-CH₃ C₆H₄-2-Cl O 3-CH₂ 0 1.463 C₆H₄-4-CH₃ C₆H₄-2-Cl O 2-CH₂ 0 1.464 C₆H₄-4-CH₃ C₆H₄-2-Cl O 4-OCH₂ 0 1.465 C₆H₄-4-CH₃ C₆H₄-2-Cl O 3-OCH₂ 0 1.466 C₆H₄-4-CH₃ C₆H₄-2-Cl O 2-OCH₂ 0 1.467 C₆H₄-4-CH₃ C₆H₄-2-Cl O 4-S 0 1.468 C₆H₄-4-CH₃ C₆H₄-2-Cl O 3-S 0 1.469 C₆H₄-4-CH₃ C₆H₄-2-Cl O 2-S 0 1.470 C₆H₄-4-CH₃ C₆H₄-2-Cl O 4-S(O) 0 1.471 C₆H₄-4-CH₃ C₆H₄-2-Cl O 3-S(O) 0 1.472 C₆H₄-4-CH₃ C₆H₄-2-Cl O 2-S(O) 0 1.473 C₆H₄-4-CH₃ C₆H₄-2-Cl O 4-C(O) 0 1.474 C₆H₃-4-CH₃ C₆H₄-2-Cl O 4-C(O) 1 Bd 3-Ar₁ 1.475 C₆H₃-4-CH₃ C₆H₄-2-Cl O 4-C(O) 1 3-C(O) 1.476 C₆H₃-4-CH₃ C₆H₄-2-Cl O 4-C(O) 1 3-S(O₂) 1.477 C₆H₃-4-CH₃ C₆H₄-2-Cl O 3-C(O) 0 1.478 C₆H₃-4-CH₃ C₆H₄-2-Cl O 3-C(O) 1 Bd 4-Ar₁ 1.479 C₆H₃-4-CH₃ C₆H₄-2-Cl O 3-C(O) 1 4-S(O₂) 1.480 C₆H₄-4-CH₃ C₆H₄-2-Cl O 2-C(O) 0 1.481 C₆H₃-4-CH₃ C₆H₄-2-Cl O 2-C(O) 1 Bd 3-Ar₁ 1.482 C₆H₃-4-CH₃ C₆H₄-2-Cl O 2-C(O) 1 3-C(O) 1.483 C₆H₃-4-CH₃ C₆H₄-2-Cl O 2-C(O) 1 3-S(O₂) 1.484 C₆H₄-4-CH₃ C₆H₄-2-Cl S 4-CH₂ 0 1.485 C₆H₄-4-CH₃ C₆H₄-2-Cl S 3-CH₂ 0 1.486 C₆H₄-4-CH₃ C₆H₄-2-Cl S 2-CH₂ 0 1.487 C₆H₄-4-CH₃ C₆H₄-2-Cl S 4-OCH₂ 0 1.488 C₆H₄-4-CH₃ C₆H₄-2-Cl S 3-OCH₂ 0 1.489 C₆H₄-4-CH₃ C₆H₄-2-Cl S 2-OCH₂ 0 1.490 C₆H₄-4-CH₃ C₆H₄-2-Cl S 4-S 0 1.491 C₆H₄-4-CH₃ C₆H₄-2-Cl S 3-S 0 1.492 C₆H₄-4-CH₃ C₆H₄-2-Cl S 2-S 0 1.493 C₆H₄-4-CH₃ C₆H₄-2-Cl S 4-S(O) 0 1.494 C₆H₄-4-CH₃ C₆H₄-2-Cl S 3-S(O) 0 1.495 C₆H₄-4-CH₃ C₆H₄-2-Cl S 2-S(O) 0 1.496 C₆H₄-4-CH₃ C₆H₄-2-Cl S 4-C(O) 0 1.497 C₆H₃-4-CH₃ C₆H₄-2-Cl S 4-C(O) 1 Bd 3-Ar₁ 1.498 C₆H₃-4-CH₃ C₆H₄-2-Cl S 4-C(O) 1 3-C(O) 1.499 C₆H₃-4-CH₃ C₆H₄-2-Cl S 4-C(O) 1 3-S(O₂) 1.500 C₆H₃-4-CH₃ C₆H₄-2-Cl S 3-C(O) 0 1.501 C₆H₃-4-CH₃ C₆H₄-2-Cl S 3-C(O) 1 Bd 4-Ar₁ 1.502 C₆H₃-4-CH₃ C₆H₄-2-Cl S 3-C(O) 1 4-S(O₂) 1.503 C₆H₄-4-CH₃ C₆H₄-2-Cl S 2-C(O) 0 1.504 C₆H₃-4-CH₃ C₆H₄-2-Cl S 2-C(O) 1 Bd 3-Ar₁ 1.505 C₆H₃-4-CH₃ C₆H₄-2-Cl S 2-C(O) 1 3-C(O) 1.506 C₆H₃-4-CH₃ C₆H₄-2-Cl S 2-C(O) 1 3-S(O₂) 1.507 C₆H₄-4-CH₃ C₆H₄-2-CF₃ O 4-CH₂ 0 1.508 C₆H₄-4-CH₃ C₆H₄-2-CF₃ O 3-CH₂ 0 1.509 C₆H₄-4-CH₃ C₆H₄-2-CF₃ O 2-CH₂ 0 1.510 C₆H₄-4-CH₃ C₆H₄-2-CF₃ O 4-OCH₂ 0 1.511 C₆H₄-4-CH₃ C₆H₄-2-CF₃ O 3-OCH₂ 0 1.512 C₆H₄-4-CH₃ C₆H₄-2-CF₃ O 2-OCH₂ 0 1.513 C₆H₄-4-CH₃ C₆H₄-2-CF₃ O 4-S 0 1.514 C₆H₄-4-CH₃ C₆H₄-2-CF₃ O 3-S 0 1.515 C₆H₄-4-CH₃ C₆H₄-2-CF₃ O 2-S 0 1.516 C₆H₄-4-CH₃ C₆H₄-2-CF₃ O 4-S(O) 0 1.517 C₆H₄-4-CH₃ C₆H₄-2-CF₃ O 3-S(O) 0 1.518 C₆H₄-4-CH₃ C₆H₄-2-CF₃ O 2-S(O) 0 1.519 C₆H₄-4-CH₃ C₆H₄-2-CF₃ O 4-C(O) 0 1.520 C₆H₃-4-CH₃ C₆H₄-2-CF₃ O 4-C(O) 1 Bd 3-Ar₁ 1.521 C₆H₃-4-CH₃ C₆H₄-2-CF₃ O 4-C(O) 1 3-C(O) 1.522 C₆H₃-4-CH₃ C₆H₄-2-CF₃ O 4-C(O) 1 3-S(O₂) 1.523 C₆H₃-4-CH₃ C₆H₄-2-CF₃ O 3-C(O) 0 1.524 C₆H₃-4-CH₃ C₆H₄-2-CF₃ O 3-C(O) 1 Bd 4-Ar₁ 1.525 C₆H₃-4-CH₃ C₆H₄-2-CF₃ O 3-C(O) 1 4-S(O₂) 1.526 C₆H₄-4-CH₃ C₆H₄-2-CF₃ O 2-C(O) 0 1.527 C₆H₃-4-CH₃ C₆H₄-2-CF₃ O 2-C(O) 1 Bd 3-Ar₁ 1.528 C₆H₃-4-CH₃ C₆H₄-2-CF₃ O 2-C(O) 1 3-C(O) 1.529 C₆H₃-4-CH₃ C₆H₄-2-CF₃ O 2-C(O) 1 3-S(O₂) 1.530 C₆H₄-4-CH₃ C₆H₄-2-CF₃ S 4-CH₂ 0 1.531 C₅H₄-4-CH₃ C₆H₄-2-CF₃ S 3-CH₂ 0 1.532 C₆H₄-4-CH₃ C₆H₄-2-CF₃ S 2-CH₂ 0 1.533 C₆H₄-4-CH₃ C₆H₄-2-CF₃ S 4-OCH₂ 0 1.534 C₆H₄-4-CH₃ C₆H₄-2-CF₃ S 3-OCH₂ 0 1.535 C₆H₄-4-CH₃ C₆H₄-2-CF₃ S 2-OCH₂ 0 1.536 C₆H₄-4-CH₃ C₆H₄-2-CF₃ S 4-S 0 1.537 C₆H₄-4-CH₃ C₆H₄-2-CF₃ S 3-S 0 1.538 C₆H₄-4-CH₃ C₆H₄-2-CF₃ S 2-S 0 1.539 C₆H₄-4-CH₃ C₆H₄-2-CF₃ S 4-S(O) 0 1.540 C₆H₄-4-CH₃ C₆H₄-2-CF₃ S 3-S(O) 0 1.541 C₆H₄-4-CH₃ C₆H₄-2-CF₃ S 2-S(O) 0 1.542 C₆H₄-4-CH₃ C₆H₄-2-CF₃ S 4-C(O) 0 1.543 C₆H₃-4-CH₃ C₆H₄-2-CF₃ S 4-C(O) 1 Bd 3-Ar₁ 1.544 C₆H₃-4-CH₃ C₆H₄-2-CF₃ S 4-C(O) 1 3-C(O) 1.545 C₆H₃-4-CH₃ C₆H₄-2-CF₃ S 4-C(O) 1 3-S(O₂) 1.546 C₆H₃-4-CH₃ C₆H₄-2-CF₃ S 3-C(O) 0 1.547 C₆H₃-4-CH₃ C₆H₄-2-CF₃ S 3-C(O) 1 Bd 4-Ar₁ 1.548 C₆H₃-4-CH₃ C₆H₄-2-CF₃ S 3-C(O) 1 4-S(O₂) 1.549 C₆H₄-4-CH₃ C₆H₄-2-CF₃ S 2-C(O) 0 1.550 C₆H₃-4-CH₃ C₆H₄-2-CF₃ S 2-C(O) 1 Bd 3-Ar₁ 1.551 C₆H₃-4-CH₃ C₆H₄-2-CF₃ S 2-C(O) 1 3-C(O) 1.552 C₆H₃-4-CH₃ C₆H₄-2-CF₃ S 2-C(O) 1 3-S(O₂) 1.553 C₆H₄-4-OCH₃ C₆H₅ O 4-CH₂ 0 1.554 C₆H₄-4-OCH₃ C₆H₅ O 3-CH₂ 0 1.555 C₆H₄-4-OCH₃ C₆H₅ O 2-CH₂ 0 1.556 C₆H₄-4-OCH₃ C₆H₅ O 4-OCH₂ 0 1.557 C₆H₄-4-OCH₃ C₆H₅ O 3-OCH₂ 0 1.558 C₆H₄-4-OCH₃ C₆H₅ O 2-OCH₂ 0 1.559 C₆H₄-4-OCH₃ C₆H₅ O 4-S 0 1.560 C₆H₄-4-OCH₃ C₆H₅ O 3-S 0 1.561 C₆H₄-4-OCH₃ C₆H₅ O 2-S 0 1.562 C₆H₄-4-OCH₃ C₆H₅ O 4-S(O) 0 1.563 C₆H₄-4-OCH₃ C₆H₅ O 3-S(O) 0 1.564 C₆H₄-4-OCH₃ C₆H₅ O 2-S(O) 0 1.565 C₆H₄-4-OCH₃ C₆H₅ O 4-C(O) 0 1.566 C₆H₃-4-OCH₃ C₆H₅ O 4-C(O) 1 Bd 3-Ar₁ 1.567 C₆H₃-4-OCH₃ C₆H₅ O 4-C(O) 1 3-C(O) 1.568 C₆H₃-4-OCH₃ C₆H₅ O 4-C(O) 1 3-S(O₂) 1.569 C₆H₄-4-OCH₃ C₆H₅ O 3-C(O) 0 1.570 C₆H₃-4-OCH₃ C₆H₅ O 3-C(O) 1 Bd 4-Ar₁ 1.571 C₆H₃-4-OCH₃ C₆H₅ O 3-C(O) 1 4-S(O₂) 1.572 C₆H₄-4-OCH₃ C₆H₅ O 2-C(O) 0 1.573 C₆H₃-4-OCH₃ C₆H₅ O 2-C(O) 1 Bd 3-Ar₁ 1.574 C₆H₃-4-OCH₃ C₆H₅ O 2-C(O) 1 3-C(O) 1.575 C₆H₃-4-OCH₃ C₆H₅ O 2-C(O) 1 3-S(O₂) 1.576 C₆H₄-4-OCH₃ C₆H₅ S 4-CH₂ 0 1.577 C₆H₄-4-OCH₃ C₆H₅ S 3-CH₂ 0 1.578 C₆H₄-4-OCH₃ C₆H₅ S 2-CH₂ 0 1.579 C₆H₄-4-OCH₃ C₆H₅ S 4-OCH₂ 0 1.580 C₆H₄-4-OCH₃ C₆H₅ S 3-OCH₂ 0 1.581 C₆H₄-4-OCH₃ C₆H₅ S 2-OCH₂ 0 1.582 C₆H₄-4-OCH₃ C₆H₅ S 4-S 0 1.583 C₆H₄-4-OCH₃ C₆H₅ S 3-S 0 1.584 C₆H₄-4-OCH₃ C₆H₅ S 2-S 0 1.585 C₆H₄-4-OCH₃ C₆H₅ S 4-S(O) 0 1.586 C₆H₄-4-OCH₃ C₆H₅ S 3-S(O) 0 1.587 C₆H₄-4-OCH₃ C₆H₅ S 2-S(O) 0 1.588 C₆H₄-4-OCH₃ C₆H₅ S 4-C(O) 0 1.589 C₆H₃-4-OCH₃ C₆H₅ S 4-C(O) 1 Bd 3-Ar₁ 1.590 C₆H₃-4-OCH₃ C₆H₅ S 4-C(O) 1 3-C(O) 1.591 C₆H₃-4-OCH₃ C₆H₅ S 4-C(O) 1 3-S(O₂) 1.592 C₅H₄-4-OCH₃ C₆H₅ S 3-C(O) 0 1.593 C₆H₃-4-OCH₃ C₆H₅ S 3-C(O) 1 Bd 4-Ar₁ 1.594 C₆H₃-4-OCH₃ C₆H₅ S 3-C(O) 1 4-S(O₂) 1.595 C₆H₄-4-OCH₃ C₆H₅ S 2-C(O) 0 1.596 C₆H₃-4-OCH₃ C₆H₅ S 2-C(O) 1 Bd 3-Ar₁ 1.597 C₆H₃-4-OCH₃ C₆H₅ S 2-C(O) 1 3-C(O) 1.598 C₆H₃-4-OCH₃ C₆H₅ S 2-C(O) 1 3-S(O₂) 1.599 C₆H₄-4-OCH₃ C₆H₄-2-Cl O 4-CH₂ 0 1.600 C₆H₄-4-OCH₃ C₆H₄-2-Cl O 3-CH₂ 0 1.601 C₆H₄-4-OCH₃ C₆H₄-2-Cl O 2-CH₂ 0 1.602 C₆H₄-4-OCH₃ C₆H₄-2-Cl O 4-OCH₂ 0 1.603 C₆H₄-4-OCH₃ C₆H₄-2-Cl O 3-OCH₂ 0 1.604 C₆H₄-4-OCH₃ C₆H₄-2-Cl O 2-OCH₂ 0 1.605 C₆H₄-4-OCH₃ C₆H₄-2-Cl O 4-S 0 1.606 C₆H₄-4-OCH₃ C₆H₄-2-Cl O 3-S 0 1.607 C₅H₄-4-OCH₃ C₆H₄-2-Cl O 2-S 0 1.608 C₆H₄-4-OCH₃ C₆H₄-2-Cl O 4-S(O) 0 1.609 C₆H₄-4-OCH₃ C₆H₄-2-Cl O 3-S(O) 0 1.610 C₆H₄-4-OCH₃ C₆H₄-2-Cl O 2-S(O) 0 1.611 C₆H₄-4-OCH₃ C₆H₄-2-Cl O 4-C(O) 0 1.612 C₆H₃-4-OCH₃ C₆H₄-2-Cl O 4-C(O) 1 Bd 3-Ar₁ 1.613 C₆H₃-4-OCH₃ C₆H₄-2-Cl O 4-C(O) 1 3-C(O) 1.614 C₆H₃-4-OCH₃ C₆H₄-2-Cl O 4-C(O) 1 3-S(O₂) 1.615 C₆H₄-4-OCH₃ C₆H₄-2-Cl O 3-C(O) 0 1.616 C₆H₃-4-OCH₃ C₆H₄-2-Cl O 3-C(O) 1 Bd 4-Ar₁ 1.617 C₆H₃-4-OCH₃ C₆H₄-2-Cl O 3-C(O) 1 4-S(O₂) 1.618 C₆H₄-4-OCH₃ C₆H₄-2-Cl O 2-C(O) 0 1.619 C₆H₃-4-OCH₃ C₆H₄-2-Cl O 2-C(O) 1 Bd 3-Ar₁ 1.620 C₆H₃-4-OCH₃ C₆H₄-2-Cl O 2-C(O) 1 3-C(O) 1.621 C₆H₃-4-OCH₃ C₆H₄-2-Cl O 2-C(O) 1 3-S(O₂) 1.622 C₆H₄-4-OCH₃ C₆H₄-2-Cl S 4-CH₂ 0 1.623 C₆H₄-4-OCH₃ C₆H₄-2-Cl S 3-CH₂ 0 1.624 C₆H₄-4-OCH₃ C₆H₄-2-Cl S 2-CH₂ 0 1.625 C₆H₄-4-OCH₃ C₆H₄-2-Cl S 4-OCH₂ 0 1.626 C₆H₄-4-OCH₃ C₆H₄-2-Cl S 3-OCH₂ 0 1.627 C₆H₄-4-OCH₃ C₆H₄-2-Cl S 2-OCH₂ 0 1.628 C₆H₄-4-OCH₃ C₆H₄-2-Cl S 4-S 0 1.629 C₆H₄-4-OCH₃ C₆H₄-2-Cl S 3-S 0 1.630 C₆H₄-4-OCH₃ C₆H₄-2-Cl S 2-S 0 1.631 C₆H₄-4-OCH₃ C₆H₄-2-Cl S 4-S(O) 0 1.632 C₆H₄-4-OCH₃ C₆H₄-2-Cl S 3-S(O) 0 1.633 C₆H₄-4-OCH₃ C₆H₄-2-Cl S 2-S(O) 0 1.634 C₆H₄-4-OCH₃ C₆H₄-2-Cl S 4-C(O) 0 1.635 C₆H₃-4-OCH₃ C₆H₄-2-Cl S 4-C(O) 1 Bd 3-Ar₁ 1.636 C₆H₃-4-OCH₃ C₆H₄-2-Cl S 4-C(O) 1 3-C(O) 1.637 C₆H₃-4-OCH₃ C₆H₄-2-Cl S 4-C(O) 1 3-S(O₂) 1.638 C₆H₄-4-OCH₃ C₆H₄-2-Cl S 3-C(O) 0 1.639 C₆H₃-4-OCH₃ C₆H₄-2-Cl S 3-C(O) 1 Bd 4-Ar₁ 1.640 C₆H₃-4-OCH₃ C₆H₄-2-Cl S 3-C(O) 1 4-S(O₂) 1.641 C₆H₄-4-OCH₃ C₆H₄-2-Cl S 2-C(O) 0 1.642 C₆H₃-4-OCH₃ C₆H₄-2-Cl S 2-C(O) 1 Bd 3-Ar₁ 1.643 C₆H₃-4-OCH₃ C₆H₄-2-Cl S 2-C(O) 1 3-C(O) 1.644 C₆H₃-4-OCH₃ C₆H₄-2-Cl S 2-C(O) 1 3-S(O₂) 1.645 C₆H₄-4-OCH₃ C₆H₄-2-CF₃ O 4-CH₂ 0 1.646 C₆H₄-4-OCH₃ C₆H₄-2-CF₃ O 3-CH₂ 0 1.647 C₆H₄-4-OCH₃ C₆H₄-2-CF₃ O 2-CH₂ 0 1.648 C₆H₄-4-OCH₃ C₆H₄-2-CF₃ O 4-OCH₂ 0 1.649 C₆H₄-4-OCH₃ C₆H₄-2-CF₃ O 3-OCH₂ 0 1.650 C₆H₄-4-OCH₃ C₆H₄-2-CF₃ O 2-OCH₂ 0 1.651 C₆H₄-4-OCH₃ C₆H₄-2-CF₃ O 4-S 0 1.652 C₆H₄-4-OCH₃ C₆H₄-2-CF₃ O 3-S 0 1.653 C₆H₄-4-OCH₃ C₆H₄-2-CF₃ O 2-S 0 1.654 C₆H₄-4-OCH₃ C₆H₄-2-CF₃ O 4-S(O) 0 1.655 C₆H₄-4-OCH₃ C₆H₄-2-CF₃ O 3-S(O) 0 1.656 C₆H₄-4-OCH₃ C₆H₄-2-CF₃ O 2-S(O) 0 1.657 C₆H₄-4-OCH₃ C₆H₄-2-CF₃ O 4-C(O) 0 1.658 C₆H₃-4-OCH₃ C₆H₄-2-CF₃ O 4-C(O) 1 Bd 3-Ar₁ 1.659 C₆H₃-4-OCH₃ C₆H₄-2-CF₃ O 4-C(O) 1 3-C(O) 1.660 C₆H₃-4-OCH₃ C₆H₄-2-CF₃ O 4-C(O) 1 3-S(O₂) 1.661 C₆H₄-4-OCH₃ C₆H₄-2-CF₃ O 3-C(O) 0 1.662 C₆H₃-4-OCH₃ C₆H₄-2-CF₃ O 3-C(O) 1 Bd 4-Ar₁ 1.663 C₆H₃-4-OCH₃ C₆H₄-2-CF₃ O 3-C(O) 1 4-S(O₂) 1.664 C₆H₄-4-OCH₃ C₆H₄-2-CF₃ O 2-C(O) 0 1.665 C₆H₃-4-OCH₃ C₆H₄-2-CF₃ O 2-C(O) 1 Bd 3-Ar₁ 1.666 C₆H₃-4-OCH₃ C₆H₄-2-CF₃ O 2-C(O) 1 3-C(O) 1.667 C₆H₃-4-OCH₃ C₆H₄-2-CF₃ O 2-C(O) 1 3-S(O₂) 1.668 C₆H₄-4-OCH₃ C₆H₄-2-CF₃ S 4-CH₂ 0 1.669 C₆H₄-4-OCH₃ C₆H₄-2-CF₃ S 3-CH₂ 0 1.670 C₆H₄-4-OCH₃ C₆H₄-2-CF₃ S 2-CH₂ 0 1.671 C₆H₄-4-OCH₃ C₆H₄-2-CF₃ S 4-OCH₂ 0 1.672 C₆H₄-4-OCH₃ C₆H₄-2-CF₃ S 3-OCH₂ 0 1.673 C₆H₄-4-OCH₃ C₆H₄-2-CF₃ S 2-OCH₂ 0 1.674 C₆H₄-4-OCH₃ C₆H₄-2-CF₃ S 4-S 0 1.675 C₆H₄-4-OCH₃ C₆H₄-2-CF₃ S 3-S 0 1.676 C₆H₄-4-OCH₃ C₆H₄-2-CF₃ S 2-S 0 1.677 C₆H₄-4-OCH₃ C₆H₄-2-CF₃ S 4-S(O) 0 1.678 C₆H₄-4-OCH₃ C₆H₄-2-CF₃ S 3-S(O) 0 1.679 C₆H₄-4-OCH₃ C₆H₄-2-CF₃ S 2-S(O) 0 1.680 C₆H₄-4-OCH₃ C₆H₄-2-CF₃ S 4-C(O) 0 1.681 C₆H₃-4-OCH₃ C₆H₄-2-CF₃ S 4-C(O) 1 Bd 3-Ar₁ 1.682 C₆H₃-4-OCH₃ C₆H₄-2-CF₃ S 4-C(O) 1 3-C(O) 1.683 C₆H₃-4-OCH₃ C₆H₄-2-CF₃ S 4-C(O) 1 3-S(O₂) 1.684 C₅H₄-4-OCH₃ C₆H₄-2-CF₃ S 3-C(O) 0 1.685 C₆H₃-4-OCH₃ C₆H₄-2-CF₃ S 3-C(O) 1 Bd 4-Ar₁ 1.686 C₆H₃-4-OCH₃ C₆H₄-2-CF₃ S 3-C(O) 1 4-S(O₂) 1.687 C₆H₄-4-OCH₃ C₆H₄-2-CF₃ S 2-C(O) 0 1.688 C₆H₃-4-OCH₃ C₆H₄-2-CF₃ S 2-C(O) 1 Bd 3-Ar₁ 1.689 C₆H₃-4-OCH₃ C₆H₄-2-CF₃ S 2-C(O) 1 3-C(O) 1.690 C₆H₃-4-OCH₃ C₆H₄-2-CF₃ S 2-C(O) 1 3-S(O₂) 1.691 C₆H₄-4-CF₃ C₆H₅ O 4-CH₂ 0 1.692 C₆H₄-4-CF₃ C₆H₅ O 3-CH₂ 0 1.693 C₆H₄-4-CF₃ C₆H₅ O 2-CH₂ 0 1.694 C₆H₄-4-CF₃ C₆H₅ O 4-OCH₂ 0 1.695 C₆H₄-4-CF₃ C₆H₅ O 3-OCH₂ 0 1.696 C₆H₄-4-CF₃ C₆H₅ O 2-OCH₂ 0 1.697 C₆H₄-4-CF₃ C₆H₅ O 4-S 0 1.698 C₆H₄-4-CF₃ C₆H₅ O 3-S 0 1.699 C₆H₄-4-CF₃ C₆H₅ O 2-S 0 1.700 C₆H₄-4-CF₃ C₆H₅ O 4-S(O) 0 1.701 C₆H₄-4-CF₃ C₆H₅ O 3-S(O) 0 1.702 C₆H₄-4-CF₃ C₆H₅ O 2-S(O) 0 1.703 C₆H₄-4-CF₃ C₆H₅ O 4-C(O) 0 m.p. 146° 1.704 C₆H₃-4-CF₃ C₆H₅ O 4-C(O) 1 Bd 3-Ar₁ 1.705 C₆H₃-4-CF₃ C₆H₅ O 4-C(O) 1 3-C(O) 1.706 C₆H₃-4-CF₃ C₆H₅ O 4-C(O) 1 3-S(O₂) 1.707 C₆H₄-4-CF₃ C₆H₅ O 3-C(O) 0 1.708 C₆H₃-4-CF₃ C₆H₅ O 3-C(O) 1 Bd 4-Ar₁ 1.709 C₆H₃-4-CF₃ C₆H₅ O 3-C(O) 1 4-S(O₂) 1.710 C₆H₄-4-CF₃ C₆H₅ O 2-C(O) 0 1.711 C₆H₃-4-CF₃ C₆H₅ O 2-C(O) 1 Bd 3-Ar₁ 1.712 C₆H₃-4-CF₃ C₆H₅ O 2-C(O) 1 3-C(O) 1.713 C₆H₃-4-CF₃ C₆H₅ O 2-C(O) 1 3-S(O₂) 1.714 C₅H₄-4-CF₃ C₆H₅ S 4-CH₂ 0 1.715 C₆H₄-4-CF₃ C₆H₅ S 3-CH₂ 0 1.716 C₆H₄-4-CF₃ C₆H₅ S 2-CH₂ 0 1.717 C₆H₄-4-CF₃ C₆H₅ S 4-OCH₂ 0 1.718 C₆H₄-4-CF₃ C₆H₅ S 3-OCH₂ 0 1.719 C₆H₄-4-CF₃ C₆H₅ S 2-OCH₂ 0 1.720 C₆H₄-4-CF₃ C₆H₅ S 4-S 0 1.721 C₆H₄-4-CF₃ C₆H₅ S 3-S 0 1.722 C₆H₄-4-CF₃ C₆H₅ S 2-S 0 1.723 C₆H₄-4-CF₃ C₆H₅ S 4-S(O) 0 1.724 C₆H₄-4-CF₃ C₆H₅ S 3-S(O) 0 1.725 C₆H₄-4-CF₃ C₆H₅ S 2-S(O) 0 1.726 C₆H₄-4-CF₃ C₆H₅ S 4-C(O) 0 1.727 C₆H₃-4-CF₃ C₆H₅ S 4-C(O) 1 Bd 3-Ar₁ 1.728 C₆H₃-4-CF₃ C₆H₅ S 4-C(O) 1 3-C(O) 1.729 C₆H₃-4-CF₃ C₆H₅ S 4-C(O) 1 3-S(O₂) 1.730 C₆H₄-4-CF₃ C₆H₅ S 3-C(O) 0 1.731 C₆H₃-4-CF₃ C₆H₅ S 3-C(O) 1 Bd 4-Ar₁ 1.732 C₆H₃-4-CF₃ C₆H₅ S 3-C(O) 1 4-S(O₂) 1.733 C₆H₄-4-CF₃ C₆H₅ S 2-C(O) 0 1.734 C₆H₃-4-CF₃ C₆H₅ S 2-C(O) 1 Bd 3-Ar₁ 1.735 C₆H₃-4-CF₃ C₆H₅ S 2-C(O) 1 3-C(O) 1.736 C₆H₃-4-CF₃ C₆H₅ S 2-C(O) 1 3-S(O₂) 1.737 C₆H₄-4-CF₃ C₆H₄-2-Cl O 4-CH₂ 0 1.738 C₆H₄-4-CF₃ C₆H₄-2-Cl O 3-CH₂ 0 1.739 C₆H₄-4-CF₃ C₆H₄-2-Cl O 2-CH₂ 0 1.740 C₆H₄-4-CF₃ C₆H₄-2-Cl O 4-OCH₂ 0 1.741 C₆H₄-4-CF₃ C₆H₄-2-Cl O 3-OCH₂ 0 1.742 C₆H₄-4-CF₃ C₆H₄-2-Cl O 2-OCH₂ 0 1.743 C₆H₄-4-CF₃ C₆H₄-2-Cl O 4-S 0 1.744 C₆H₄-4-CF₃ C₆H₄-2-Cl O 3-S 0 1.745 C₆H₄-4-CF₃ C₆H₄-2-Cl O 2-S 0 1.746 C₆H₄-4-CF₃ C₆H₄-2-Cl O 4-S(O) 0 1.747 C₆H₄-4-CF₃ C₆H₄-2-Cl O 3-S(O) 0 1.748 C₆H₄-4-CF₃ C₆H₄-2-Cl O 2-S(O) 0 1.749 C₆H₄-4-CF₃ C₆H₄-2-Cl O 4-C(O) 0 1.750 C₆H₃-4-CF₃ C₆H₄-2-Cl O 4-C(O) 1 Bd 3-Ar₁ 1.751 C₆H₃-4-CF₃ C₆H₄-2-Cl O 4-C(O) 1 3-C(O) 1.752 C₆H₃-4-CF₃ C₆H₄-2-Cl O 4-C(O) 1 3-S(O₂) 1.753 C₆H₄-4-CF₃ C₆H₄-2-Cl O 3-C(O) 0 1.754 C₆H₃-4-CF₃ C₆H₄-2-Cl O 3-C(O) 1 Bd 4-Ar₁ 1.755 C₆H₃-4-CF₃ C₆H₄-2-Cl O 3-C(O) 1 4-S(O₂) 1.756 C₆H₄-4-CF₃ C₆H₄-2-Cl O 2-C(O) 0 1.757 C₆H₃-4-CF₃ C₆H₄-2-Cl O 2-C(O) 1 Bd 3-Ar₁ 1.758 C₆H₃-4-CF₃ C₆H₄-2-Cl O 2-C(O) 1 3-C(O) 1.759 C₆H₃-4-CF₃ C₆H₄-2-Cl O 2-C(O) 1 3-S(O₂) 1.760 C₆H₄-4-CF₃ C₆H₄-2-Cl S 4-CH₂ 0 1.761 C₆H₄-4-CF₃ C₆H₄-2-Cl S 3-CH₂ 0 1.762 C₆H₄-4-CF₃ C₆H₄-2-Cl S 2-CH₂ 0 1.763 C₆H₄-4-CF₃ C₆H₄-2-Cl S 4-OCH₂ 0 1.764 C₆H₄-4-CF₃ C₆H₄-2-Cl S 3-OCH₂ 0 1.765 C₆H₄-4-CF₃ C₆H₄-2-Cl S 2-OCH₂ 0 1.766 C₆H₄-4-CF₃ C₆H₄-2-Cl S 4-S 0 1.767 C₆H₄-4-CF₃ C₆H₄-2-Cl S 3-S 0 1.768 C₆H₄-4-CF₃ C₆H₄-2-Cl S 2-S 0 1.769 C₆H₄-4-CF₃ C₅H₄-2-Cl S 4-S(O) 0 1.770 C₆H₄-4-CF₃ C₆H₄-2-Cl S 3-S(O) 0 1.771 C₆H₄-4-CF₃ C₆H₄-2-Cl S 2-S(O) 0 1.772 C₆H₄-4-CF₃ C₅H₄-2-Cl S 4-C(O) 0 1.773 C₆H₃-4-CF₃ C₆H₄-2-Cl S 4-C(O) 1 Bd 3-Ar₁ 1.774 C₆H₃-4-CF₃ C₆H₄-2-Cl S 4-C(O) 1 3-C(O) 1.775 C₆H₃-4-CF₃ C₆H₄-2-Cl S 4-C(O) 1 3-S(O₂) 1.776 C₆H₄-4-CF₃ C₆H₄-2-Cl S 3-C(O) 0 1.777 C₆H₃-4-CF₃ C₆H₄-2-Cl S 3-C(O) 1 Bd 4-Ar₁ 1.778 C₆H₃-4-CF₃ C₆H₄-2-Cl S 3-C(O) 1 4-S(O₂) 1.779 C₆H₄-4-CF₃ C₆H₄-2-Cl S 2-C(O) 0 1.780 C₆H₃-4-CF₃ C₆H₄-2-Cl S 2-C(O) 1 Bd 3-Ar₁ 1.781 C₆H₃-4-CF₃ C₆H₄-2-Cl S 2-C(O) 1 3-C(O) 1.782 C₆H₃-4-CF₃ C₆H₄-2-Cl S 2-C(O) 1 3-S(O₂) 1.783 C₆H₄-4-CF₃ C₆H₄-2-CF₃ O 4-CH₂ 0 1.784 C₆H₄-4-CF₃ C₆H₄-2-CF₃ O 3-CH₂ 0 1.785 C₆H₄-4-CF₃ C₆H₄-2-CF₃ O 2-CH₂ 0 1.786 C₆H₄-4-CF₃ C₆H₄-2-CF₃ O 4-OCH₂ 0 1.787 C₆H₄-4-CF₃ C₆H₄-2-CF₃ O 3-OCH₂ 0 1.788 C₆H₄-4-CF₃ C₆H₄-2-CF₃ O 2-OCH₂ 0 1.789 C₆H₄-4-CF₃ C₆H₄-2-CF₃ O 4-S 0 1.790 C₆H₄-4-CF₃ C₆H₄-2-CF₃ O 3-S 0 1.791 C₆H₄-4-CF₃ C₆H₄-2-CF₃ O 2-S 0 1.792 C₆H₄-4-CF₃ C₆H₄-2-CF₃ O 4-S(O) 0 1.793 C₆H₄-4-CF₃ C₆H₄-2-CF₃ O 3-S(O) 0 1.794 C₆H₄-4-CF₃ C₆H₄-2-CF₃ O 2-S(O) 0 1.795 C₆H₄-4-CF₃ C₆H₄-2-CF₃ O 4-C(O) 0 1.796 C₆H₃-4-CF₃ C₆H₄-2-CF₃ O 4-C(O) 1 Bd 3-Ar₁ 1.797 C₆H₃-4-CF₃ C₆H₄-2-CF₃ O 4-C(O) 1 3-C(O) 1.798 C₆H₃-4-CF₃ C₆H₄-2-CF₃ O 4-C(O) 1 3-S(O₂) 1.799 C₆H₄-4-CF₃ C₆H₄-2-CF₃ O 3-C(O) 0 1.800 C₆H₃-4-CF₃ C₆H₄-2-CF₃ O 3-C(O) 1 Bd 4-Ar₁ 1.801 C₆H₃-4-CF₃ C₆H₄-2-CF₃ O 3-C(O) 1 4-S(O₂) 1.802 C₆H₄-4-CF₃ C₆H₄-2-CF₃ O 2-C(O) 0 1.803 C₆H₃-4-CF₃ C₆H₄-2-CF₃ O 2-C(O) 1 Bd 3-Ar₁ 1.804 C₆H₃-4-CF₃ C₆H₄-2-CF₃ O 2-C(O) 1 3-C(O) 1.805 C₆H₃-4-CF₃ C₆H₄-2-CF₃ O 2-C(O) 1 3-S(O₂) 1.806 C₆H₄-4-CF₃ C₆H₄-2-CF₃ S 4-CH₂ 0 1.807 C₆H₄-4-CF₃ C₆H₄-2-CF₃ S 3-CH₂ 0 1.808 C₆H₄-4-CF₃ C₆H₄-2-CF₃ S 2-CH₂ 0 1.809 C₆H₄-4-CF₃ C₆H₄-2-CF₃ S 4-OCH₂ 0 1.810 C₆H₄-4-CF₃ C₆H₄-2-CF₃ S 3-OCH₂ 0 1.811 C₆H₄-4-CF₃ C₆H₄-2-CF₃ S 2-OCH₂ 0 1.812 C₆H₄-4-CF₃ C₆H₄-2-CF₃ S 4-S 0 1.813 C₆H₄-4-CF₃ C₆H₄-2-CF₃ S 3-S 0 1.814 C₆H₄-4-CF₃ C₆H₄-2-CF₃ S 2-S 0 1.815 C₆H₄-4-CF₃ C₆H₄-2-CF₃ S 4-S(O) 0 1.816 C₆H₄-4-CF₃ C₆H₄-2-CF₃ S 3-S(O) 0 1.817 C₆H₄-4-CF₃ C₆H₄-2-CF₃ S 2-S(O) 0 1.818 C₆H₄-4-CF₃ C₆H₄-2-CF₃ S 4-C(O) 0 1.819 C₆H₃-4-CF₃ C₆H₄-2-CF₃ S 4-C(O) 1 Bd 3-Ar₁ 1.820 C₆H₃-4-CF₃ C₆H₄-2-CF₃ S 4-C(O) 1 3-C(O) 1.821 C₆H₃-4-CF₃ C₆H₄-2-CF₃ S 4-C(O) 1 3-S(O₂) 1.822 C₆H₄-4-CF₃ C₆H₄-2-CF₃ S 3-C(O) 0 1.823 C₆H₃-4-CF₃ C₆H₄-2-CF₃ S 3-C(O) 1 Bd 4-Ar₁ 1.824 C₆H₃-4-CF₃ C₆H₄-2-CF₃ S 3-C(O) 1 4-S(O₂) 1.825 C₆H₄-4-CF₃ C₆H₄-2-CF₃ S 2-C(O) 0 1.826 C₆H₃-4-CF₃ C₆H₄-2-CF₃ S 2-C(O) 1 Bd 3-Ar₁ 1.827 C₆H₃-4-CF₃ C₆H₄-2-CF₃ S 2-C(O) 1 3-C(O) 1.828 C₆H₃-4-CF₃ C₆H₄-2-CF₃ S 2-C(O) 1 3-S(O₂) 1.829 C₆H₄-4-OCF₃ C₆H₅ O 4-CH₂ 0 1.830 C₆H₄-4-OCF₃ C₆H₅ O 3-CH₂ 0 1.831 C₆H₄-4-OCF₃ C₆H₅ O 2-CH₂ 0 1.832 C₆H₄-4-OCF₃ C₆H₅ O 4-OCH₂ 0 1.833 C₆H₄-4-OCF₃ C₆H₅ O 3-OCH₂ 0 1.834 C₆H₄-4-OCF₃ C₆H₅ O 2-OCH₂ 0 1.835 C₆H₄-4-OCF₃ C₆H₅ O 4-S 0 1.836 C₆H₄-4-OCF₃ C₆H₅ O 3-S 0 1.837 C₆H₄-4-OCF₃ C₆H₅ O 2-S 0 1.838 C₆H₄-4-OCF₃ C₆H₅ O 4-S(O) 0 1.839 C₆H₄-4-OCF₃ C₆H₅ O 3-S(O) 0 1.840 C₆H₄-4-OCF₃ C₆H O 2-S(O) 0 1.841 C₅H₄-4-OCF₃ C₆H₅ O 4-C(O) 0 1.842 C₆H₃-4-OCF₃ C₆H₅ O 4-C(O) 1 Bd 3-Ar₁ 1.843 C₆H₃-4-OCF₃ C₆H₅ O 4-C(O) 1 3-C(O) 1.844 C₆H₃-4-OCF₃ C₆H₅ O 4-C(O) 1 3-S(O₂) 1.845 C₆H₄-4-OCF₃ C₆H₅ O 3-C(O) 0 1.846 C₆H₃-4-OCF₃ C₆H₅ O 3-C(O) 1 Bd 4-Ar₁ 1.847 C₆H₃-4-OCF₃ C₆H₅ O 3-C(O) 1 4-S(O₂) 1.848 C₆H₄-4-OCF₃ C₆H₅ O 2-C(O) 0 1.849 C₆H₃-4-OCF₃ C₆H₅ O 2-C(O) 1 Bd 3-Ar₁ 1.850 C₆H₃-4-OCF₃ C₆H₅ O 2-C(O) 1 3-C(O) 1.851 C₆H₃-4-OCF₃ C₆H₅ O 2-C(O) 1 3-S(O₂) 1.852 C₆H₄-4-OCF₃ C₆H₅ S 4-CH₂ 0 1.853 C₆H₄-4-OCF₃ C₆H₅ S 3-CH₂ 0 1.854 C₆H₄-4-OCF₃ C₆H₅ S 2-CH₂ 0 1.855 C₆H₄-4-OCF₃ C₆H₅ S 4-OCH₂ 0 1.856 C₆H₄-4-OCF₃ C₆H₅ S 3-OCH₂ 0 1.857 C₆H₄-4-OCF₃ C₆H₅ S 2-OCH₂ 0 1.858 C₆H₄-4-OCF₃ C₆H₅ S 4-S 0 1.859 C₆H₄-4-OCF₃ C₆H₅ S 3-S 0 1.860 C₆H₄-4-OCF₃ C₆H₅ S 2-S 0 1.861 C₆H₄-4-OCF₃ C₆H₅ S 4-S(O) 0 1.862 C₆H₄-4-OCF₃ C₆H₅ S 3-S(O) 0 1.863 C₆H₄-4-OCF₃ C₆H₅ S 2-S(O) 0 1.864 C₆H₄-4-OCF₃ C₆H₅ S 4-C(O) 0 1.865 C₆H₃-4-OCF₃ C₆H₅ S 4-C(O) 1 Bd 3-Ar₁ 1.866 C₆H₃-4-OCF₃ C₆H₅ S 4-C(O) 1 3-C(O) 1.867 C₆H₃-4-OCF₃ C₆H₅ S 4-C(O) 1 3-S(O₂) 1.868 C₆H₄-4-OCF₃ C₆H₅ S 3-C(O) 0 1.869 C₆H₃-4-OCF₃ C₆H₅ S 3-C(O) 1 Bd 4-Ar₁ 1.870 C₆H₃-4-OCF₃ C₆H₅ S 3-C(O) 1 4-S(O₂) 1.871 C₆H₄-4-OCF₃ C₆H₅ S 2-C(O) 0 1.872 C₆H₃-4-OCF₃ C₆H₅ S 2-C(O) 1 Bd 3-Ar₁ 1.873 C₆H₃-4-OCF₃ C₆H₅ S 2-C(O) 1 3-C(O) 1.874 C₆H₃-4-OCF₃ C₆H₅ S 2-C(O) 1 3-S(O₂) 1.875 C₆H₄-4-OCF₃ C₆H₄-2-Cl O 4-CH₂ 0 1.876 C₅H₄-4-OCF₃ C₆H₄-2-Cl O 3-CH₂ 0 1.877 C₆H₄-4-OCF₃ C₆H₄-2-Cl O 2-CH₂ 0 1.878 C₆H₄-4-OCF₃ C₆H₄-2-Cl O 4-OCH₂ 0 1.879 C₆H₄-4-OCF₃ C₆H₄-2-Cl O 3-OCH₂ 0 1.880 C₆H₄-4-OCF₃ C₆H₄-2-Cl O 2-OCH₂ 0 1.881 C₆H₄-4-OCF₃ C₆H₄-2-Cl O 4-S 0 1.882 C₆H₄-4-OCF₃ C₆H₄-2-Cl O 3-S 0 1.883 C₆H₄-4-OCF₃ C₆H₄-2-Cl O 2-S 0 1.884 C₆H₄-4-OCF₃ C₆H₄-2-Cl O 4-S(O) 0 1.885 C₆H₄-4-OCF₃ C₆H₄-2-Cl O 3-S(O) 0 1.886 C₆H₄-4-OCF₃ C₆H₄-2-Cl O 2-S(O) 0 1.887 C₆H₄-4-OCF₃ C₆H₄-2-Cl O 4-C(O) 0 1.888 C₆H₃-4-OCF₃ C₆H₄-2-Cl O 4-C(O) 1 Bd 3-Ar₁ 1.889 C₆H₃-4-OCF₃ C₆H₄-2-Cl O 4-C(O) 1 3-C(O) 1.890 C₆H₃-4-OCF₃ C₆H₄-2-Cl O 4-C(O) 1 3-S(O₂) 1.891 C₆H₄-4-OCF₃ C₆H₄-2-Cl O 3-C(O) 0 1.892 C₆H₃-4-OCF₃ C₆H₄-2-Cl O 3-C(O) 1 Bd 4-Ar₁ 1.893 C₆H₃-4-OCF₃ C₆H₄-2-Cl O 3-C(O) 1 4-S(O₂) 1.894 C₆H₄-4-OCF₃ C₆H₄-2-Cl O 2-C(O) 0 1.895 C₆H₃-4-OCF₃ C₆H₄-2-Cl O 2-C(O) 1 Bd 3-Ar₁ 1.896 C₆H₃-4-OCF₃ C₆H₄-2-Cl O 2-C(O) 1 3-C(O) 1.897 C₆H₃-4-OCF₃ C₆H₄-2-Cl O 2-C(O) 1 3-S(O₂) 1.898 C₆H₄-4-OCF₃ C₆H₄-2-Cl S 4-CH₂ 0 1.899 C₆H₄-4-OCF₃ C₆H₄-2-Cl S 3-CH₂ 0 1.900 C₆H₄-4-OCF₃ C₆H₄-2-Cl S 2-CH₂ 0 1.901 C₆H₄-4-OCF₃ C₆H₄-2-Cl S 4-OCH₂ 0 1.902 C₆H₄-4-OCF₃ C₆H₄-2-Cl S 3-OCH₂ 0 1.903 C₆H₄-4-OCF₃ C₆H₄-2-Cl S 2-OCH₂ 0 1.904 C₆H₄-4-OCF₃ C₆H₄-2-Cl S 4-S 0 1.905 C₆H₄-4-OCF₃ C₆H₄-2-Cl S 3-S 0 1.906 C₆H₄-4-OCF₃ C₆H₄-2-Cl S 2-S 0 1.907 C₆H₄-4-OCF₃ C₆H₄-2-Cl S 4-S(O) 0 1.908 C₆H₄-4-OCF₃ C₆H₄-2-Cl S 3-S(O) 0 1.909 C₆H₄-4-OCF₃ C₆H₄-2-Cl S 2-S(O) 0 1.910 C₆H₄-4-OCF₃ C₆H₄-2-Cl S 4-C(O) 0 1.911 C₆H₃-4-OCF₃ C₆H₄-2-Cl S 4-C(O) 1 Bd 3-Ar₁ 1.912 C₆H₃-4-OCF₃ C₆H₄-2-Cl S 4-C(O) 1 3-C(O) 1.913 C₆H₃-4-OCF₃ C₆H₄-2-Cl S 4-C(O) 1 3-S(O₂) 1.914 C₆H₄-4-OCF₃ C₆H₄-2-Cl S 3-C(O) 0 1.915 C₆H₃-4-OCF₃ C₆H₄-2-Cl S 3-C(O) 1 Bd 4-Ar₁ 1.916 C₆H₃-4-OCF₃ C₆H₄-2-Cl S 3-C(O) 1 4-S(O₂) 1.917 C₆H₄-4-OCF₃ C₆H₄-2-Cl S 2-C(O) 0 1.918 C₆H₃-4-OCF₃ C₆H₄-2-Cl S 2-C(O) 1 Bd 3-Ar₁ 1.919 C₆H₃-4-OCF₃ C₆H₄-2-Cl S 2-C(O) 1 3-C(O) 1.920 C₆H₃-4-OCF₃ C₆H₄-2-Cl S 2-C(O) 1 3-S(O₂) 1.921 C₆H₄-4-OCF₃ C₆H₄-2-CF₃ O 4-CH₂ 0 1.922 C₆H₄-4-OCF₃ C₆H₄-2-CF₃ O 3-CH₂ 0 1.923 C₆H₄-4-OCF₃ C₆H₄-2-CF₃ O 2-CH₂ 0 1.924 C₆H₄-4-OCF₃ C₆H₄-2-CF₃ O 4-OCH₂ 0 1.925 C₆H₄-4-OCF₃ C₆H₄-2-CF₃ O 3-OCH₂ 0 1.926 C₆H₄-4-OCF₃ C₆H₄-2-CF₃ O 2-OCH₂ 0 1.927 C₆H₄-4-OCF₃ C₆H₄-2-CF₃ O 4-S 0 1.928 C₆H₄-4-OCF₃ C₆H₄-2-CF₃ O 3-S 0 1.929 C₆H₄-4-OCF₃ C₆H₄-2-CF₃ O 2-S 0 1.930 C₆H₄-4-OCF₃ C₆H₄-2-CF₃ O 4-S(O) 0 1.931 C₆H₄-4-OCF₃ C₆H₄-2-CF₃ O 3-S(O) 0 1.932 C₆H₄-4-OCF₃ C₆H₄-2-CF₃ O 2-S(O) 0 1.933 C₆H₄-4-OCF₃ C₆H₄-2-CF₃ O 4-C(O) 0 1.934 C₆H₃-4-OCF₃ C₆H₄-2-CF₃ O 4-C(O) 1 Bd 3-Ar₁ 1.935 C₆H₃-4-OCF₃ C₆H₄-2-CF₃ O 4-C(O) 1 3-C(O) 1.936 C₆H₃-4-OCF₃ C₆H₄-2-CF₃ O 4-C(O) 1 3-S(O₂) 1.937 C₆H₄-4-OCF₃ C₆H₄-2-CF₃ O 3-C(O) 0 1.938 C₆H₃-4-OCF₃ C₆H₄-2-CF₃ O 3-C(O) 1 Bd 4-Ar₁ 1.939 C₆H₃-4-OCF₃ C₆H₄-2-CF₃ O 3-C(O) 1 4-S(O₂) 1.940 C₆H₄-4-OCF₃ C₆H₄-2-CF₃ O 2-C(O) 0 1.941 C₆H₃-4-OCF₃ C₆H₄-2-CF₃ O 2-C(O) 1 Bd 3-Ar₁ 1.942 C₆H₃-4-OCF₃ C₆H₄-2-CF₃ O 2-C(O) 1 3-C(O) 1.943 C₆H₃-4-OCF₃ C₆H₄-2-CF₃ O 2-C(O) 1 3-S(O₂) 1.944 C₆H₄-4-OCF₃ C₆H₄-2-CF₃ S 4-CH₂ 0 1.945 C₆H₄-4-OCF₃ C₆H₄-2-CF₃ S 3-CH₂ 0 1.946 C₆H₄-4-OCF₃ C₆H₄-2-CF₃ S 2-CH₂ 0 1.947 C₆H₄-4-OCF₃ C₆H₄-2-CF₃ S 4-OCH₂ 0 1.948 C₆H₄-4-OCF₃ C₆H₄-2-CF₃ S 3-OCH₂ 0 1.949 C₆H₄-4-OCF₃ C₆H₄-2-CF₃ S 2-OCH₂ 0 1.950 C₆H₄-4-OCF₃ C₆H₄-2-CF₃ S 4-S 0 1.951 C₆H₄-4-OCF₃ C₆H₄-2-CF₃ S 3-S 0 1.952 C₆H₄-4-OCF₃ C₆H₄-2-CF₃ S 2-S 0 1.953 C₆H₄-4-OCF₃ C₆H₄-2-CF₃ S 4-S(O) 0 1.954 C₆H₄-4-OCF₃ C₆H₄-2-CF₃ S 3-S(O) 0 1.955 C₆H₄-4-OCF₃ C₆H₄-2-CF₃ S 2-S(O) 0 1.956 C₆H₄-4-OCF₃ C₆H₄-2-CF₃ S 4-C(O) 0 1.957 C₆H₃-4-OCF₃ C₆H₄-2-CF₃ S 4-C(O) 1 Bd 3-Ar₁ 1.958 C₆H₃-4-OCF₃ C₆H₄-2-CF₃ S 4-C(O) 1 3-C(O) 1.959 C₆H₃-4-OCF₃ C₆H₄-2-CF₃ S 4-C(O) 1 3-S(O₂) 1.960 C₆H₄-4-OCF₃ C₆H₄-2-CF₃ S 3-C(O) 0 1.961 C₆H₃-4-OCF₃ C₆H₄-2-CF₃ S 3-C(O) 1 Bd 4-Ar₁ 1.962 C₆H₃-4-OCF₃ C₆H₄-2-CF₃ S 3-C(O) 1 4-S(O₂) 1.963 C₆H₄-4-OCF₃ C₆H₄-2-CF₃ S 2-C(O) 0 1.964 C₆H₃-4-OCF₃ C₆H₄-2-CF₃ S 2-C(O) 1 Bd 3-Ar₁ 1.965 C₆H₃-4-OCF₃ C₆H₄-2-CF₃ S 2-C(O) 1 3-C(O) 1.966 C₆H₃-4-OCF₃ C₆H₄-2-CF₃ S 2-C(O) 1 3-S(O₂) 1.967 C₆H₄-4-t-C₄H₉ C₆H₅ O 4-CH₂ 0 1.968 C₆H₄-4-t-C₄H₉ C₆H₅ O 3-CH₂ 0 1.969 C₆H₄-4-t-C₄H₉ C₆H₅ O 2-CH₂ 0 1.970 C₆H₄-4-t-C₄H₉ C₆H₅ O 4-OCH₂ 0 1.971 C₆H₄-4-t-C₄H₉ C₆H₅ O 3-OCH₂ 0 1.972 C₆H₄-4-t-C₄H₉ C₆H₅ O 2-OCH₂ 0 1.973 C₆H₄-4-t-C₄H₉ C₆H₅ O 4-S 0 1.974 C₆H₄-4-t-C₄H₉ C₆H₅ O 3-S 0 1.975 C₆H₄-4-t-C₄H₉ C₆H₅ O 2-S 0 1.976 C₆H₄-4-t-C₄H₉ C₆H₅ O 4-S(O) 0 1.977 C₆H₄-4-t-C₄H₉ C₆H₅ O 3-S(O) 0 1.978 C₆H₄-4-t-C₄H₉ C₆H₅ O 2-S(O) 0 1.979 C₆H₄-4-t-C₄H₉ C₆H₅ O 4-C(O) 0 1.980 C₆H₃-4-t-C₄H₉ C₆H₅ O 4-C(O) 1 Bd 3-Ar₁ 1.981 C₆H₃-4-t-C₄H₉ C₆H₅ O 4-C(O) 1 3-C(O) 1.982 C₆H₃-4-t-C₄H₉ C₆H₅ O 4-C(O) 1 3-S(O₂) 1.983 C₆H₄-4-t-C₄H₉ C₆H₅ O 3-C(O) 0 1.984 C₆H₃-4-t-C₄H₉ C₆H₅ O 3-C(O) 1 Bd 4-Ar₁ 1.985 C₆H₃-4-t-C₄H₉ C₆H₅ O 3-C(O) 1 4-S(O₂) 1.986 C₆H₄-4-t-C₄H₉ C₆H₅ O 2-C(O) 0 1.987 C₆H₃-4-t-C₄H₉ C₆H₅ O 2-C(O) 1 Bd 3-Ar₁ 1.988 C₆H₃-4-t-C₄H₉ C₆H₅ O 2-C(O) 1 3-C(O) 1.989 C₆H₃-4-t-C₄H₉ C₆H₅ O 2-C(O) 1 3-S(O₂) 1.990 C₆H₄-4-t-C₄H₉ C₆H₅ S 4-CH₂ 0 1.991 C₆H₄-4-t-C₄H₉ C₆H₅ S 3-CH₂ 0 1.992 C₆H₄-4-t-C₄H₉ C₆H₅ S 2-CH₂ 0 1.993 C₆H₄-4-t-C₄H₉ C₆H₅ S 4-OCH₂ 0 1.994 C₆H₄-4-t-C₄H₉ C₆H₅ S 3-OCH₂ 0 1.995 C₆H₄-4-t-C₄H₉ C₆H₅ S 2-OCH₂ 0 1.996 C₆H₄-4-t-C₄H₉ C₆H₅ S 4-S 0 1.997 C₆H₄-4-t-C₄H₉ C₆H₅ S 3-S 0 1.998 C₆H₄-4-t-C₄H₉ C₆H₅ S 2-S 0 1.999 C₆H₄-4-t-C₄H₉ C₆H₅ S 4-S(O) 0 1.1000 C₆H₄-4-t-C₄H₉ C₆H₅ S 3-S(O) 0 1.1001 C₆H₄-4-t-C₄H₉ C₆H₅ S 2-S(O) 0 1.1002 C₆H₄-4-t-C₄H₉ C₆H₅ S 4-C(O) 0 1.1003 C₆H₃-4-t-C₄H₉ C₆H₅ S 4-C(O) 1 Bd 3-Ar₁ 1.1004 C₆H₃-4-t-C₄H₉ C₆H₅ S 4-C(O) 1 3-C(O) 1.1005 C₆H₃-4-t-C₄H₉ C₆H₅ S 4-C(O) 1 3-S(O₂) 1.1006 C₆H₄-4-t-C₄H₉ C₆H₅ S 3-C(O) 0 1.1007 C₆H₃-4-t-C₄H₉ C₆H₅ S 3-C(O) 1 Bd 4-Ar₁ 1.1008 C₆H₃-4-t-C₄H₉ C₆H₅ S 3-C(O) 1 4-S(O₂) 1.1009 C₆H₄-4-t-C₄H₉ C₆H₅ S 2-C(O) 0 1.1010 C₆H₃-4-t-C₄H₉ C₆H₅ S 2-C(O) 1 Bd 3-Ar₁ 1.1011 C₆H₃-4-t-C₄H₉ C₆H₅ S 2-C(O) 1 3-C(O) 1.1012 C₆H₃-4-t-C₄H₉ C₆H₅ S 2-C(O) 1 3-S(O₂) 1.1013 C₆H₄-4-t-C₄H₉ C₆H₄-2-Cl O 4-CH₂ 0 1.1014 C₆H₄-4-t-C₄H₉ C₆H₄-2-Cl O 3-CH₂ 0 1.1015 C₆H₄-4-t-C₄H₉ C₆H₄-2-Cl O 2-CH₂ 0 1.1016 C₆H₄-4-t-C₄H₉ C₆H₄-2-Cl O 4-OCH₂ 0 1.1017 C₆H₄-4-t-C₄H₉ C₆H₄-2-Cl O 3-OCH₂ 0 1.1018 C₆H₄-4-t-C₄H₉ C₆H₄-2-Cl O 2-OCH₂ 0 1.1019 C₆H₄-4-t-C₄H₉ C₆H₄-2-Cl O 4-S 0 1.1020 C₆H₄-4-t-C₄H₉ C₆H₄-2-Cl O 3-S 0 1.1021 C₆H₄-4-t-C₄H₉ C₆H₄-2-Cl O 2-S 0 1.1022 C₆H₄-4-t-C₄H₉ C₆H₄-2-Cl O 4-S(O) 0 1.1023 C₆H₄-4-t-C₄H₉ C₆H₄-2-Cl O 3-S(O) 0 1.1024 C₆H₄-4-t-C₄H₉ C₆H₄-2-Cl O 2-S(O) 0 1.1025 C₆H₄-4-t-C₄H₉ C₆H₄-2-Cl O 4-C(O) 0 1.1026 C₆H₃-4-t-C₄H₉ C₆H₄-2-Cl O 4-C(O) 1 Bd 3-Ar₁ 1.1027 C₆H₃-4-t-C₄H₉ C₆H₄-2-Cl O 4-C(O) 1 3-C(O) 1.1028 C₆H₃-4-t-C₄H₉ C₆H₄-2-Cl O 4-C(O) 1 3-S(O₂) 1.1029 C₆H₄-4-t-C₄H₉ C₆H₄-2-Cl O 3-C(O) 0 1.1030 C₆H₃-4-t-C₄H₉ C₆H₄-2-Cl O 3-C(O) 1 Bd 4-Ar₁ 1.1031 C₆H₃-4-t-C₄H₉ C₆H₄-2-Cl O 3-C(O) 1 4-S(O₂) 1.1032 C₆H₄-4-t-C₄H₉ C₆H₄-2-Cl O 2-C(O) 0 1.1033 C₆H₃-4-t-C₄H₉ C₆H₄-2-Cl O 2-C(O) 1 Bd 3-Ar₁ 1.1034 C₆H₃-4-t-C₄H₉ C₆H₄-2-Cl O 2-C(O) 1 3-C(O) 1.1035 C₆H₃-4-t-C₄H₉ C₆H₄-2-Cl O 2-C(O) 1 3-S(O₂) 1.1036 C₆H₄-4-t-C₄H₉ C₆H₄-2-Cl S 4-CH₂ 0 1.1037 C₆H₄-4-t-C₄H₉ C₆H₄-2-Cl S 3-CH₂ 0 1.1038 C₆H₄-4-t-C₄H₉ C₆H₄-2-Cl S 2-CH₂ 0 1.1039 C₆H₄-4-t-C₄H₉ C₆H₄-2-Cl S 4-OCH₂ 0 1.1040 C₆H₄-4-t-C₄H₉ C₆H₄-2-Cl S 3-OCH₂ 0 1.1041 C₆H₄-4-t-C₄H₉ C₆H₄-2-Cl S 2-OCH₂ 0 1.1042 C₆H₄-4-t-C₄H₉ C₆H₄-2-Cl S 4-S 0 1.1043 C₆H₄-4-t-C₄H₉ C₆H₄-2-Cl S 3-S 0 1.1044 C₅H₄-4-t-C₄H₉ C₆H₄-2-Cl S 2-S 0 1.1045 C₆H₄-4-t-C₄H₉ C₆H₄-2-Cl S 4-S(O) 0 1.1046 C₆H₄-4-t-C₄H₉ C₆H₄-2-Cl S 3-S(O) 0 1.1047 C₆H₄-4-t-C₄H₉ C₆H₄-2-Cl S 2-S(O) 0 1.1048 C₆H₄-4-t-C₄H₉ C₆H₄-2-Cl S 4-C(O) 0 1.1049 C₆H₃-4-t-C₄H₉ C₆H₄-2-Cl S 4-C(O) 1 Bd 3-Ar₁ 1.1050 C₆H₃-4-t-C₄H₉ C₆H₄-2-Cl S 4-C(O) 1 3-C(O) 1.1051 C₆H₃-4-t-C₄H₉ C₆H₄-2-Cl S 4-C(O) 1 3-S(O₂) 1.1052 C₆H₄-4-t-C₄H₉ C₆H₄-2-Cl S 3-C(O) 0 1.1053 C₆H₃-4-t-C₄H₉ C₆H₄-2-Cl S 3-C(O) 1 Bd 4-Ar₁ 1.1054 C₆H₃-4-t-C₄H₉ C₅H₄-2-Cl S 3-C(O) 1 4-S(O₂) 1.1055 C₆H₄-4-t-C₄H₉ C₆H₄-2-Cl S 2-C(O) 0 1.1056 C₆H₃-4-t-C₄H₉ C₆H₄-2-Cl S 2-C(O) 1 Bd 3-Ar₁ 1.1057 C₅H₃-4-t-C₄H₉ C₆H₄-2-Cl S 2-C(O) 1 3-C(O) 1.1058 C₆H₃-4-t-C₄H₉ C₆H₄-2-Cl S 2-C(O) 1 3-S(O₂) 1.1059 C₆H₄-4-t-C₄H₉ C₆H₄-2-CF₃ O 4-CH₂ 0 1.1060 C₆H₄-4-t-C₄H₉ C₆H₄-2-CF₃ O 3-CH₂ 0 1.1061 C₆H₄-4-t-C₄H₉ C₆H₄-2-CF₃ O 2-CH₂ 0 1.1062 C₆H₄-4-t-C₄H₉ C₆H₄-2-CF₃ O 4-OCH₂ 0 1.1063 C₆H₄-4-t-C₄H₉ C₆H₄-2-CF₃ O 3-OCH₂ 0 1.1064 C₆H₄-4-t-C₄H₉ C₆H₄-2-CF₃ O 2-OCH₂ 0 1.1065 C₆H₄-4-t-C₄H₉ C₆H₄-2-CF₃ O 4-S 0 1.1066 C₆H₄-4-t-C₄H₉ C₆H₄-2-CF₃ O 3-S 0 1.1067 C₆H₄-4-t-C₄H₉ C₆H₄-2-CF₃ O 2-S 0 1.1068 C₆H₄-4-t-C₄H₉ C₆H₄-2-CF₃ O 4-S(O) 0 1.1069 C₆H₄-4-t-C₄H₉ C₆H₄-2-CF₃ O 3-S(O) 0 1.1070 C₆H₄-4-t-C₄H₉ C₆H₄-2-CF₃ O 2-S(O) 0 1.1071 C₆H₄-4-t-C₄H₉ C₆H₄-2-CF₃ O 4-C(O) 0 1.1072 C₆H₃-4-t-C₄H₉ C₆H₄-2-CF₃ O 4-C(O) 1 Bd 3-Ar₁ 1.1073 C₅H₃-4-t-C₄H₉ C₆H₄-2-CF₃ O 4-C(O) 1 3-C(O) 1.1074 C₆H₃-4-t-C₄H₉ C₆H₄-2-CF₃ O 4-C(O) 1 3-S(O₂) 1.1075 C₆H₄-4-t-C₄H₉ C₆H₄-2-CF₃ O 3-C(O) 0 1.1076 C₆H₃-4-t-C₄H₉ C₆H₄-2-CF₃ O 3-C(O) 1 Bd 4-Ar₁ 1.1077 C₆H₃-4-t-C₄H₉ C₆H₄-2-CF₃ O 3-C(O) 1 4-S(O₂) 1.1078 C₆H₄-4-t-C₄H₉ C₆H₄-2-CF₃ O 2-C(O) 0 1.1079 C₆H₃-4-t-C₄H₉ C₆H₄-2-CF₃ O 2-C(O) 1 Bd 3-Ar₁ 1.1080 C₆H₃-4-t-C₄H₉ C₆H₄-2-CF₃ O 2-C(O) 1 3-C(O) 1.1081 C₆H₃-4-t-C₄H₉ C₆H₄-2-CF₃ O 2-C(O) 1 3-S(O₂) 1.1082 C₆H₄-4-t-C₄H₉ C₆H₄-2-CF₃ S 4-CH₂ 0 1.1083 C₆H₄-4-t-C₄H₉ C₆H₄-2-CF₃ S 3-CH₂ 0 1.1084 C₆H₄-4-t-C₄H₉ C₆H₄-2-CF₃ S 2-CH₂ 0 1.1085 C₆H₄-4-t-C₄H₉ C₆H₄-2-CF₃ S 4-OCH₂ 0 1.1086 C₆H₄-4-t-C₄H₉ C₆H₄-2-CF₃ S 3-OCH₂ 0 1.1087 C₆H₄-4-t-C₄H₉ C₆H₄-2-CF₃ S 2-OCH₂ 0 1.1088 C₆H₄-4-t-C₄H₉ C₆H₄-2-CF₃ S 4-S 0 1.1089 C₆H₄-4-t-C₄H₉ C₆H₄-2-CF₃ S 3-S 0 1.1090 C₆H₄-4-t-C₄H₉ C₆H₄-2-CF₃ S 2-S 0 1.1091 C₆H₄-4-t-C₄H₉ C₆H₄-2-CF₃ S 4-S(O) 0 1.1092 C₆H₄-4-t-C₄H₉ C₆H₄-2-CF₃ S 3-S(O) 0 1.1093 C₆H₄-4-t-C₄H₉ C₆H₄-2-CF₃ S 2-S(O) 0 1.1094 C₆H₄-4-t-C₄H₉ C₆H₄-2-CF₃ S 4-C(O) 0 1.1095 C₆H₃-4-t-C₄H₉ C₆H₄-2-CF₃ S 4-C(O) 1 Bd 3-Ar₁ 1.1096 C₆H₃-4-t-C₄H₉ C₆H₄-2-CF₃ S 4-C(O) 1 3-C(O) 1.1097 C₆H₃-4-t-C₄H₉ C₆H₄-2-CF₃ S 4-C(O) 1 3-S(O₂) 1.1098 C₆H₄-4-t-C₄H₉ C₆H₄-2-CF₃ S 3-C(O) 0 1.1099 C₆H₃-4-t-C₄H₉ C₆H₄-2-CF₃ S 3-C(O) 1 Bd 4-Ar₁ 1.1100 C₆H₃-4-t-C₄H₉ C₆H₄-2-CF₃ S 3-C(O) 1 4-S(O₂) 1.1101 C₆H₄-4-t-C₄H₉ C₆H₄-2-CF₃ S 2-C(O) 0 1.1102 C₆H₃-4-t-C₄H₉ C₆H₄-2-CF₃ S 2-C(O) 1 Bd 3-Ar₁ 1.1103 C₆H₃-4-t-C₄H₉ C₆H₄-2-CF₃ S 2-C(O) 1 3-C(O) 1.1104 C₆H₃-4-t-C₄H₉ C₆H₄-2-CF₃ S 2-C(O) 1 3-S(O₂) 1.1105 3-C₅H₄N C₆H₅ O 4-CH₂ 0 1.1106 3-C₅H₄N C₆H₅ O 3-CH₂ 0 1.1107 3-C₅H₄N C₆H₅ O 2-CH₂ 0 1.1108 3-C₅H₄N C₆H₅ O 4-OCH₂ 0 1.1109 3-C₅H₄N C₆H₅ O 3-OCH₂ 0 1.1110 3-C₅H₄N C₆H₅ O 2-OCH₂ 0 1.1111 3-C₅H₄N C₆H₅ O 4-S 0 1.1112 3-C₅H₄N C₆H₅ O 3-S 0 1.1113 3-C₅H₄N C₆H₅ O 2-S 0 1.1114 3-C₅H₄N C₆H₅ O 4-S(O) 0 1.1115 3-C₅H₄N C₆H₅ O 3-S(O) 0 1.1116 3-C₅H₄N C₆H₅ O 2-S(O) 0 1.1117 3-C₅H₄N C₆H₅ O 4-C(O) 0 1.1118 3-C₅H₄N C₆H₅ O 3-C(O) 0 1.1119 3-C₅H₄N C₆H₅ O 2-C(O) 0 1.1120 3-C₅H₄N C₆H₅ S 4-CH₂ 0 1.1121 3-C₅H₄N C₆H₅ S 3-CH₂ 0 1.1122 3-C₅H₄N C₆H₅ S 2-CH₂ 0 1.1123 3-C₅H₄N C₆H₅ S 4-OCH₂ 0 1.1124 3-C₅H₄N C₆H₅ S 3-OCH₂ 0 1.1125 3-C₅H₄N C₆H₅ S 2-OCH₂ 0 1.1126 3-C₅H₄N C₆H₅ S 4-S 0 1.1127 3-C₅H₄N C₆H₅ S 3-S 0 1.1128 3-C₅H₄N C₆H₅ S 2-S 0 1.1129 3-C₅H₄N C₆H₅ S 4-S(O) 0 1.1130 3-C₅H₄N C₆H₅ S 3-S(O) 0 1.1131 3-C₅H₄N C₆H₅ S 2-S(O) 0 1.1132 3-C₅H₄N C₆H₅ S 4-C(O) 0 1.1133 3-C₅H₄N C₆H₅ S 3-C(O) 0 1.1134 3-C₅H₄N C₆H₅ S 2-C(O) 0 1.1135 3-C₅H₄N C₆H₄-2-Cl O 4-CH₂ 0 1.1136 3-C₅H₄N C₆H₄-2-Cl O 3-CH₂ 0 1.1137 3-C₅H₄N C₆H₄-2-Cl O 2-CH₂ 0 1.1138 3-C₅H₄N C₆H₄-2-Cl O 4-OCH₂ 0 1.1139 3-C₅H₄N C₆H₄-2-Cl O 3-OCH₂ 0 1.1140 3-C₅H₄N C₆H₄-2-Cl O 2-OCH₂ 0 1.1141 3-C₅H₄N C₆H₄-2-Cl O 4-S 0 1.1142 3-C₅H₄N C₆H₄-2-Cl O 3-S 0 1.1143 3-C₅H₄N C₆H₄-2-Cl O 2-S 0 1.1144 3-C₅H₄N C₆H₄-2-Cl O 4-S(O) 0 1.1145 3-C₅H₄N C₆H₄-2-Cl O 3-S(O) 0 1.1146 3-C₅H₄N C₆H₄-2-Cl O 2-S(O) 0 1.1147 3-C₅H₄N C₆H₄-2-Cl O 4-C(O) 0 1.1148 3-C₅H₄N C₆H₄-2-Cl O 3-C(O) 0 1.1149 3-C₅H₄N C₆H₄-2-Cl O 2-C(O) 0 1.1150 3-C₅H₄N C₆H₄-2-Cl S 4-CH₂ 0 1.1151 3-C₅H₄N C₆H₄-2-Cl S 3-CH₂ 0 1.1152 3-C₅H₄N C₆H₄-2-Cl S 2-CH₂ 0 1.1153 3-C₅H₄N C₆H₄-2-Cl S 4-OCH₂ 0 1.1154 3-C₅H₄N C₆H₄-2-Cl S 3-OCH₂ 0 1.1155 3-C₅H₄N C₆H₄-2-Cl S 2-OCH₂ 0 1.1156 3-C₅H₄N C₆H₄-2-Cl S 4-S 0 1.1157 3-C₅H₄N C₆H₄-2-Cl S 3-S 0 1.1158 3-C₅H₄N C₆H₄-2-Cl S 2-S 0 1.1159 3-C₅H₄N C₆H₄-2-Cl S 4-S(O) 0 1.1160 3-C₅H₄N C₆H₄-2-Cl S 3-S(O) 0 1.1161 3-C₅H₄N C₆H₄-2-Cl S 2-S(O) 0 1.1162 3-C₅H₄N C₆H₄-2-Cl S 4-C(O) 0 1.1163 3-C₅H₄N C₆H₄-2-Cl S 3-C(O) 0 1.1164 3-C₅H₄N C₆H₄-2-Cl S 2-C(O) 0 1.1165 3-C₅H₄N C₆H₄-2-CF₃ O 4-CH₂ 0 1.1166 3-C₅H₄N C₆H₄-2-CF₃ O 3-CH₂ 0 1.1167 3-C₅H₄N C₆H₄-2-CF₃ O 2-CH₂ 0 1.1168 3-C₅H₄N C₆H₄-2-CF₃ O 4-OCH₂ 0 1.1169 3-C₅H₄N C₆H₄-2-CF₃ O 3-OCH₂ 0 1.1170 3-C₆H₄N C₆H₄-2-CF₃ O 2-OCH₂ 0 1.1171 3-C₅H₄N C₆H₄-2-CF₃ O 4-S 0 1.1172 3-C₅H₄N C₆H₄-2-CF₃ O 3-S 0 1.1173 3-C₅H₄N C₆H₄-2-CF₃ O 2-S 0 1.1174 3-C₅H₄N C₆H₄-2-CF₃ O 4-S(O) 0 1.1175 3-C₅H₄N C₆H₄-2-CF₃ O 3-S(O) 0 1.1176 3-C₅H₄N C₆H₄-2-CF₃ O 2-S(O) 0 1.1177 3-C₅H₄N C₆H₄-2-CF₃ O 4-C(O) 0 1.1178 3-C₅H₄N C₆H₄-2-CF₃ O 3-C(O) 0 1.1179 3-C₅H₄N C₆H₄-2-CF₃ O 2-C(O) 0 1.1180 3-C₅H₄N C₆H₄-2-CF₃ S 4-CH₂ 0 1.1181 3-C₅H₄N C₆H₄-2-CF₃ S 3-CH₂ 0 1.1182 3-C₅H₄N C₆H₄-2-CF₃ S 2-CH₂ 0 1.1183 3-C₅H₄N C₆H₄-2-CF₃ S 4-OCH₂ 0 1.1184 3-C₅H₄N C₆H₄-2-CF₃ S 3-OCH₂ 0 1.1185 3-C₅H₄N C₆H₄-2-CF₃ S 2-OCH₂ 0 1.1186 3-C₅H₄N C₆H₄-2-CF₃ S 4-S 0 1.1187 3-C₅H₄N C₆H₄-2-CF₃ S 3-S 0 1.1188 3-C₅H₄N C₆H₄-2-CF₃ S 2-S 0 1.1189 3-C₅H₄N C₆H₄-2-CF₃ S 4-S(O) 0 1.1190 3-C₅H₄N C₆H₄-2-CF₃ S 3-S(O) 0 1.1191 3-C₅H₄N C₆H₄-2-CF₃ S 2-S(O) 0 1.1192 3-C₅H₄N C₆H₄-2-CF₃ S 4-C(O) 0 1.1193 3-C₅H₄N C₆H₄-2-CF₃ S 3-C(O) 0 1.1194 3-C₆H₄N C₆H₄-2-CF₃ S 2-C(O) 0 1.1195 2-C₄H₃S C₆H₅ O 4-CH₂ 0 1.1196 2-C₄H₃S C₆H₅ O 3-CH₂ 0 1.1197 2-C₄H₃S C₆H₅ O 2-CH₂ 0 1.1198 2-C₄H₃S C₆H₅ O 4-OCH₂ 0 1.1199 2-C₄H₃S C₆H₅ O 3-OCH₂ 0 1.1200 2-C₄H₃S C₆H₅ O 2-OCH₂ 0 1.1201 2-C₄H₃S C₆H₅ O 4-S 0 1.1202 2-C₄H₃S C₆H₅ O 3-S 0 1.1203 2-C₄H₃S C₆H₅ O 2-S 0 1.1204 2-C₄H₃S C₆H₅ O 4-S(O) 0 1.1205 2-C₄H₃S C₆H₅ O 3-S(O) 0 1.1206 2-C₄H₃S C₆H₅ O 2-S(O) 0 1.1207 2-C₄H₃S C₆H₅ O 4-C(O) 0 1.1208 2-C₄H₃S C₆H₅ O 3-C(O) 0 1.1209 2-C₄H₃S C₆H₅ O 2-C(O) 0 1.1210 2-C₄H₃S C₆H₅ S 4-CH₂ 0 1.1211 2-C₄H₃S C₆H₅ S 3-CH₂ 0 1.1212 2-C₄H₃S C₆H₅ S 2-CH₂ 0 1.1213 2-C₄H₃S C₆H₅ S 4-OCH₂ 0 1.1214 2-C₄H₃S C₆H₅ S 3-OCH₂ 0 1.1215 2-C₄H₃S C₆H₅ S 2-OCH₂ 0 1.1216 2-C₄H₃S C₆H₅ S 4-S 0 1.1217 2-C₄H₃S C₆H₅ S 3-S 0 1.1218 2-C₄H₃S C₆H₅ S 2-S 0 1.1219 2-C₄H₃S C₆H₅ S 4-S(O) 0 1.1220 2-C₄H₃S C₆H₅ S 3-S(O) 0 1.1221 2-C₄H₃S C₆H₅ S 2-S(O) 0 1.1222 2-C₄H₃S C₆H₅ S 4-C(O) 0 1.1223 2-C₄H₃S C₆H₅ S 3-C(O) 0 1.1224 2-C₄H₃S C₆H₅ S 2-C(O) 0 1.1225 2-C₄H₃S C₆H₄-2-Cl O 4-CH₂ 0 1.1226 2-C₄H₃S C₆H₄-2-Cl O 3-CH₂ 0 1.1227 2-C₄H₃S C₆H₄-2-Cl O 2-CH₂ 0 1.1228 2-C₄H₃S C₆H₄-2-Cl O 4-OCH₂ 0 1.1229 2-C₄H₃S C₆H₄-2-Cl O 3-OCH₂ 0 1.1230 2-C₄H₃S C₆H₄-2-Cl O 2-OCH₂ 0 1.1231 2-C₄H₃S C₆H₄-2-Cl O 4-S 0 1.1232 2-C₄H₃S C₆H₄-2-Cl O 3-S 0 1.1233 2-C₄H₃S C₆H₄-2-Cl O 2-S 0 1.1234 2-C₄H₃S C₆H₄-2-Cl O 4-S(O) 0 1.1235 2-C₄H₃S C₆H₄-2-Cl O 3-S(O) 0 1.1236 2-C₄H₃S C₆H₄-2-Cl O 2-S(O) 0 1.1237 2-C₄H₃S C₆H₄-2-Cl O 4-C(O) 0 1.1238 2-C₄H₃S C₆H₄-2-Cl O 3-C(O) 0 1.1239 2-C₄H₃S C₆H₄-2-Cl O 2-C(O) 0 1.1240 2-C₄H₃S C₆H₄-2-Cl S 4-CH₂ 0 1.1241 2-C₄H₃S C₆H₄-2-Cl S 3-CH₂ 0 1.1242 2-C₄H₃S C₆H₄-2-Cl S 2-CH₂ 0 1.1243 2-C₄H₃S C₆H₄-2-Cl S 4-OCH₂ 0 1.1244 2-C₄H₃S C₆H₄-2-Cl S 3-OCH₂ 0 1.1245 2-C₄H₃S C₆H₄-2-Cl S 2-OCH₂ 0 1.1246 2-C₄H₃S C₆H₄-2-Cl S 4-S 0 1.1247 2-C₄H₃S C₆H₄-2-Cl S 3-S 0 1.1248 2-C₄H₃S C₆H₄-2-Cl S 2-S 0 1.1249 2-C₄H₃S C₆H₄-2-Cl S 4-S(O) 0 1.1250 2-C₄H₃S C₆H₄-2-Cl S 3-S(O) 0 1.1251 2-C₄H₃S C₆H₄-2-Cl S 2-S(O) 0 1.1252 2-C₄H₃S C₆H₄-2-Cl S 4-C(O) 0 1.1253 2-C₄H₃S C₆H₄-2-Cl S 3-C(O) 0 1.1254 2-C₄H₃S C₆H₄-2-Cl S 2-C(O) 0 1.1255 2-C₄H₃S C₆H₄-2-CF₃ O 4-CH₂ 0 1.1256 2-C₄H₃S C₆H₄-2-CF₃ O 3-CH₂ 0 1.1257 2-C₄H₃S C₆H₄-2-CF₃ O 2-CH₂ 0 1.1258 2-C₄H₃S C₆H₄-2-CF₃ O 4-OCH₂ 0 1.1259 2-C₄H₃S C₆H₄-2-CF₃ O 3-OCH₂ 0 1.1260 2-C₄H₃S C₆H₄-2-CF₃ O 2-OCH₂ 0 1.1261 2-C₄H₃S C₆H₄-2-CF₃ O 4-S 0 1.1262 2-C₄H₃S C₆H₄-2-CF₃ O 3-S 0 1.1263 2-C₄H₃S C₆H₄-2-CF₃ O 2-S 0 1.1264 2-C₄H₃S C₆H₄-2-CF₃ O 4-S(O) 0 1.1265 2-C₄H₃S C₆H₄-2-CF₃ O 3-S(O) 0 1.1266 2-C₄H₃S C₆H₄-2-CF₃ O 2-S(O) 0 1.1267 2-C₄H₃S C₆H₄-2-CF₃ O 4-C(O) 0 1.1268 2-C₄H₃S C₆H₄-2-CF₃ O 3-C(O) 0 1.1269 2-C₄H₃S C₆H₄-2-CF₃ O 2-C(O) 0 1.1270 2-C₄H₃S C₆H₄-2-CF₃ S 4-CH₂ 0 1.1271 2-C₄H₃S C₆H₄-2-CF₃ S 3-CH₂ 0 1.1272 2-C₄H₃S C₆H₄-2-CF₃ S 2-CH₂ 0 1.1273 2-C₄H₃S C₆H₄-2-CF₃ S 4-OCH₂ 0 1.1274 2-C₄H₃S C₆H₄-2-CF₃ S 3-OCH₂ 0 1.1275 2-C₄H₃S C₆H₄-2-CF₃ S 2-OCH₂ 0 1.1276 2-C₄H₃S C₆H₄-2-CF₃ S 4-S 0 1.1277 2-C₄H₃S C₆H₄-2-CF₃ S 3-S 0 1.1278 2-C₄H₃S C₆H₄-2-CF₃ S 2-S 0 1.1279 2-C₄H₃S C₆H₄-2-CF₃ S 4-S(O) 0 1.1280 2-C₄H₃S C₆H₄-2-CF₃ S 3-S(O) 0 1.1281 2-C₄H₃S C₆H₄-2-CF₃ S 2-S(O) 0 1.1282 2-C₄H₃S C₆H₄-2-CF₃ S 4-C(O) 0 1.1283 2-C₄H₃S C₆H₄-2-CF₃ S 3-C(O) 0 1.1284 2-C₄H₃S C₆H₄-2-CF₃ S 2-C(O) 0

TABLE 2

No. Q₁ Ar₂ phys. data 2.1 4-CH(OH) C₆H₄-2-CF₃ m.p. 72° 2.2 4-C(CH₃)(OH) C₆H₄-2-CF₃ m.p. 108-10° 2.3 4-C(NOCH₃) C₆H₄-2-CF₃ m.p. 61° 2.4 4-C(O) C₆H₃-2-Cl-5-CH₃ m.p. 148-50° 2.5 4-C(O) C₆H₃-2,5-Cl₂ m.p. 160-2° 2.6 4-C(O) C₆H₂-2-Br-4,5-F₂ m.p. 69-71°

Biological Examples 1. In-Vivo Test on Trichostrongylus colubriformis and Haemonchus contortus on Mongolian Gerbils (Meiones unguiculatus) Using Peroral Application

Six to eight week old Mongolian gerbils are infected by artificial feeding with ca. 2000 third instar larvae each of T. colubriformis and H. contortus. 6 days after infection, the gerbils are lightly anaesthetised with N₂O and treated by peroral application with the test compounds, dissolved in a mixture of 2 parts DMSO and 1 part polyethylene glycol (PEG 300), in quantities of 100, 32 and 10-0.1 mg/kg. On day 9 (3 days after treatment), when most of the H. contortus that are still present are late 4th instar larvae and most of the T. colubdformis are immature adults, the gerbils are killed in order to count the worms. The efficacy is calculated as the % reduction of the number of worms in each gerbil, compared with the geometric average of number of worms from 8 infected and untreated gerbils.

In this test, a vast reduction in nematode infestation is achieved with compounds of formula I, especially from Table 1. In particular, compounds 1.59 and 1.105 effect a 100% reduction in Trichostrongylus infestation even at doses of 32 mg/kg.

To examine the insecticidal and/or acaricidal activity of the compounds of formula I on animals and plants, the following test methods may be used.

2. Insecticidal Stomach Toxicant Activity on Spodoptera littoralils

Potted cotton plants at the 5-leaf stage are each sprayed with an acetonic/aqueous test solution containing 1, 3, 12.5 or 50 ppm of the compound to be tested.

After drying of the spray deposit, the plants are colonised with ca. 30 larvae (L₁ stage) of Spodoptera littoralis. Two plants are used per test compound and per test species. The test is carried out at ca. 24° C. and at 60% relative humidity. Evaluations and intermediate evaluations on moribund animals, larvae and feeding damage are made after 24, 48 and 72 h.

3. Activity on Phytotoxic Acarids

OP-Sensitive Tetranychus urticae

The primary leaves of bean plants (Phaseolus vulgais) are covered 16 hours before the test with a mass-cultivated piece of leaf infested with T. urticae. After removing the piece of leaf, the plants that are infested with all stages of the mites are sprayed to drip point with a test solution containing either 0.2, 0.4 or 1.6 ppm of the compound to be tested. The temperature in the greenhouse is ca. 25° C. After 7 days, an evaluation of the percentage of mobile stages (adults and nymphs) and of eggs is made under a microscope.

4. Activity on L₁ Larvae of Lucilia sedcata

1 ml of an aqueous suspension of the active substance to be tested is admixed with 3 ml of a special larvae growth medium at ca. 50° C., so that a homogenate of either 250 or 125 ppm of active ingredient content is obtained. Ca. 30 Lucilia larvae (L₁) are used in each test tube sample. After 4 days, the mortality rate is determined.

5. Acaricidal Activity on Boophilus microplus (Biarra Strain)

A piece of sticky tape is attached horizontally to a PVC sheet, so that 10 fully engorged female ticks of Boophilus microplus (Biarra strain) can be adhered thereto by their backs, side by side, in a row. Using an injection needle, 1 μl of a liquid is injected into each tick. The liquid is a 1:1 mixture of polyethylene glycol and acetone and it contains, dissolved therein, a certain amount of active ingredient chosen from 1, 0.1 or 0.01 μg per tick. Control animals are given an injection without active ingredient. After treatment, the animals are kept under normal conditions in an insectarium at ca. 28° C. and at 80% relative humidity until oviposition takes place and the larvae have hatched from the eggs of the control animals. The activity of a tested substance is determined by IR₉₀, i.e. an evaluation is made of the dosage of active ingredient at which 9 out of 10 female ticks (=90%) lay eggs that are infertile even after 30 days.

6. In Vitro Efficacy on Engorged Female Boophilus microbus (BIARRA):

4×10 engorged female ticks of the OP-resistant BIARRA strain are adhered to a sticky strip and covered for 1 hour with a cotton-wool ball soaked in an emulsion or suspension of the test compound in concentrations of 500, 125, 31 and 8 ppm respectively. Evaluation takes place 28 days later based on mortality, oviposition and hatched larvae.

An indication of the activity of the test compounds is shown by the number of females that

-   -   die quickly before laying eggs,     -   survive for some time without laying eggs,     -   lay eggs in which no embryos are formed,     -   lay eggs in which embryos form, from which no larvae hatch, and     -   lay eggs in which embryos form, from which larvae normally hatch         within 26 to 27 days.

7. Contact Action on Aphis craccivora

Pea seedlings that have been infested with all stages of development of the aphids are sprayed with a solution of active ingredient prepared from an emulsion concentrate, the solution containing 50, 25 or 12.5 ppm of active ingredient, as desired. After 3 days, an evaluation is made of more than 80% of aphids that are either dead or have fallen off. Only at this level of activity is a preparation classified as effective.

8. Larvicidal Activity on Aedes aegypti

A sufficient quantity of a 0.1% acetonic solution of the active ingredient for a chosen concentration of 10, 3.3 or 1.6 ppm to be attained, is added by pipette to the surface of 150 ml of water in a container. After evaporation of the acetone, the container is covered with ca. 30-403-day old Aedes larvae. After 1, 2 and 5 days, the mortality is tested.

9. In Vivo Efficacy on Adult Ctenoceohalides felis on Domestic Cats After Oral Treatment

The test substances are given orally to domestic cats in a gelatin capsule before or after feeding, the dose varying between 0.5 and 20 mg/kg. On days 1, 3, 7 and 10 after treatment, each cat is exposed to 100 fleas (ca. 50 male and ca. 50 female), depending on the result of previous flea colonisation. The efficacy (in % reduction in flea numbers) is based on the number of living fleas found after combing for 10 minutes one day after each new flea colonisation, whereby the efficacy in % corresponds to the arithmetic average of the number of living fleas on control animals minus the number of living fleas on the treated animals, divided by the arithmetic average of the number of living fleas on control animals and multiplied by 100.

The dying fleas found in the cat cages and by combing are collected, placed in an incubator at 28° C. and 70% relative humidity and after 24 hours are tested for survival/mortality. If the majority of dying fleas die, the test compound is regarded as a flea adulticide, and if the majority survive, the test compound shows “knock-down” activity.

10. In Vivo Efficacy on Adult Ctenocephalides felis on Domestic Cats After Spot-On Treatment

The test substances are given to domestic cats as spot-on treatment, the dose varying between 0.5 and 10 mg/kg. On days 1, 3, 7 and 10 after treatment, each cat is exposed to 100 fleas (ca. 50 male and ca. 50 female), depending on the result of previous flea colonisation.

The efficacy (in % reduction in flea numbers) is based on the number of living fleas found after combing for 10 minutes one day after each new flea colonisation, whereby the efficacy in % corresponds to the arithmetic average of the number of living fleas on control animals minus the number of living fleas on the treated animals, divided by the arithmetic average of the number of living fleas on control animals and multiplied by 100.

The dying fleas found in the cat cages and by combing are collected, placed in an incubator at 28° C. and 70% relative humidity and after 24 hours are tested for survival/mortality. If the majority of dying fleas die, the test compound is regarded as a flea adulticide, and if the majority survive, the test compound shows “knock-down” activity.

11. In Vitro Efficacy on Nymphs of Amblyomma hebraeum

About 5 fasting nymphs are placed in a polystyrene test tube containing 2 ml of the test compound in solution, suspension or emulsion.

After immersion for 10 minutes, and shaking for 2×10 seconds on a vortex mixer, the test tubes are blocked up with a tight wad of cotton wool and rotated. As soon as all the liquid has been soaked up by the cotton wool ball, it is pushed half-way into the test tube which is still being rotated, so that most of the liquid is squeezed out of the cotton-wool ball and flows into a Petri dish below.

The test tubes are then kept at room temperature in a room with daylight until evaluated. After 14 days, the test tubes are immersed in a beaker of boiling water. If the ticks begin to move in reaction to the heat, the test substance is inactive at the tested concentration, otherwise the ticks are regarded as dead and the test substances regarded as active at the tested concentration. All substances are tested in a concentration range of 0.1 to 100 ppm.

12. Activity Against Dermanyssus gallinae

2 to 3 ml of a solution containing 10 ppm active ingredient, and ca. 200 mites (Dermanyssus gallinae) at different stages of development are added to a glass container which is open at the top. Then the container is closed with a wad of cotton wool, shaken for 10 minutes until the mites are completely wet, and then inverted briefly so that the remaining test solution can be absorbed by the cotton wool. After 3 days, the mortality of the mites is determined by counting the dead individuals and indicated as a percentage.

13. Activity Against Musca domestica

A sugar cube is treated with a solution of the test substance in such a way that the concentration of test substance in the sugar, after drying over night, is 250 ppm. The cube treated in this way is placed on an aluminium dish with wet cotton wool and 10 adult Musca domestica of an OP-resistant strain, covered with a beaker and incubated at 25° C. The mortality rate is determined after 24 hours. 

1. A compound of formula I:

wherein each of Ar₁ and Ar₂, independently of one another, signify phenyl that is either unsubstituted or substituted one or more times, whereby the substituents may be independent of one another and are selected from the group consisting of halogen, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₈-alkoxy, halo-C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, C₁-C₆-alkylthio, halo-C₁-C₆-alkylthio, C₁-C₆-alkylcarbonyl, halo-C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylaminocarbonyl, and di-C₁-C₆-alkylaminocarbonyl; Q₁ signifies C(O); R₃ signifies hydrogen or C₁-C₂-alkyl; each of R₄, R₅, R₆, R₇, and R₈, independently of one another, signify hydrogen, halogen, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, or C₃-C₆-cycloalkyl; W signifies O or N(R₉); R₉ signifies hydrogen or C₁-C₂-alkyl; a signifies 1, 2, 3, or 4; b signifies 0, 1, 2, 3, or 4; and n signifies
 0. 2. A compound of formula I according to claim 1, wherein each of Ar₁ and Ar₂, independently of one another, signify phenyl that is either unsubstituted or substituted one or more times, whereby the substituents may be independent of one another and are selected from the group consisting of halogen, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₁-C₆-alkoxy, and halo-C₁-C₆-alkoxy; Q₁ signifies C(O); R₃ signifies hydrogen; each of R₄, R₅, R₆, R₇, and R₈, independently of one another, signify hydrogen, halogen, C₁-C₆-alkyl, or halo-C₁-C₆-alkyl; W signifies O; R₉ signifies methyl; a signifies 1; b signifies 0 or 1; and n is
 0. 3. A compound of formula I according to claim 1 wherein the compound is 4-Benzoyl-N-[1-cyano-1-methyl-2-(2-trifluoromethylphenoxy)-ethyl]-benzamide.
 4. A composition for the control of parasites, comprising at least one compound of formula I according to claim 1 and one or more carriers or dispersants.
 5. A method of controlling parasites in an animal in need thereof, comprising administering to said animal a parasiticidal amount of a compound of formula I as defined in claim
 1. 6. The method of claim 5, whereby said animals are warm-blooded animals.
 7. A method for controlling pests comprising administering to said pests an effective amount of a compound of formula I as defined in claim 1 to kill said pests.
 8. A compound of formula I according to claim 1, wherein R₃ signifies hydrogen.
 9. A compound of formula I according to claim 1, wherein each of R₄, R₅, R₆, R₇, and R₈, independently of one another, is hydrogen, halogen, C₁-C₆-alkyl, or halo-C₁-C₆-alkyl.
 10. A compound of formula I according to claim 1, wherein W is O.
 11. A compound of formula I according to claim 1, wherein a is
 1. 12. A compound of formula I according to claim 1, wherein b is 0 or
 1. 